CA2566215C - Cyclohexyl-1,4-diamines substituted by acid derivatives - Google Patents
Cyclohexyl-1,4-diamines substituted by acid derivatives Download PDFInfo
- Publication number
- CA2566215C CA2566215C CA2566215A CA2566215A CA2566215C CA 2566215 C CA2566215 C CA 2566215C CA 2566215 A CA2566215 A CA 2566215A CA 2566215 A CA2566215 A CA 2566215A CA 2566215 C CA2566215 C CA 2566215C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- benzyl
- cyclohexylcarbamoyl
- dimethylamino
- 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
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- 239000002253 acid Substances 0.000 title description 26
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- 238000002360 preparation method Methods 0.000 claims abstract description 22
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- 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 abstract description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 5
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- -1 benzodioxolanyl Chemical group 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 41
- 229920006395 saturated elastomer Polymers 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000001544 thienyl group Chemical group 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 125000002541 furyl group Chemical group 0.000 claims description 22
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 19
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 19
- 125000001041 indolyl group Chemical group 0.000 claims description 19
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 18
- 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 13
- 229940080818 propionamide Drugs 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000003444 anaesthetic effect Effects 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 208000000094 Chronic Pain Diseases 0.000 claims description 7
- 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 7
- 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 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 208000004880 Polyuria Diseases 0.000 claims description 6
- 230000035619 diuresis Effects 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000011260 co-administration Methods 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
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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 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003158 myorelaxant agent Substances 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
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- 239000002858 neurotransmitter agent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
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- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 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 3
- BGVGKXHMOSEQOL-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(O)=O)CCC1(N(C)C)CC1=CC=CC(F)=C1 BGVGKXHMOSEQOL-UHFFFAOYSA-N 0.000 claims description 3
- BAKUUYYCWZZNKV-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(O)=O)CCC1(N(C)C)CC1=CC=CC(C)=C1 BAKUUYYCWZZNKV-UHFFFAOYSA-N 0.000 claims description 3
- HYXSVLJLQQHZQW-UHFFFAOYSA-N [3-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-3-oxopropyl]carbamic acid Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(NC(=O)CCNC(O)=O)CC1 HYXSVLJLQQHZQW-UHFFFAOYSA-N 0.000 claims description 3
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
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- 125000003367 polycyclic group Chemical group 0.000 claims description 3
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 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
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 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 2
- NNGOTRFRZOVEPS-UHFFFAOYSA-N 4-chloro-n-[2-[4-[1-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]ethyl]benzamide Chemical compound C1CC(NC(=O)C(C)(C)OC=2C=CC(CCNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl NNGOTRFRZOVEPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 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 2
- QCWWMKNJKWEDCU-UHFFFAOYSA-N C(C1=CC=CC=C1)C1(CCC(CC1)NC(=O)C(CC(C)C)NC(=O)CNC(O)=O)N1CCCCC1.C(C1=CC=CC=C1)OC(NC(C)C(NC1CCC(CC1)(N(C)C)CC1=CC(=CC=C1)Cl)=O)=O Chemical compound C(C1=CC=CC=C1)C1(CCC(CC1)NC(=O)C(CC(C)C)NC(=O)CNC(O)=O)N1CCCCC1.C(C1=CC=CC=C1)OC(NC(C)C(NC1CCC(CC1)(N(C)C)CC1=CC(=CC=C1)Cl)=O)=O QCWWMKNJKWEDCU-UHFFFAOYSA-N 0.000 claims description 2
- FGJYIQSDGPUFKV-UHFFFAOYSA-N C(C1=CC=CC=C1)C1(CCC(CC1)NC(=O)C(CO)NC(O)=O)N1CCCCC1.C(C1=CC=CC=C1)OC(NC(C)C(NC1CCC(CC1)(C1=CC=CC=C1)N1CCOCC1)=O)=O Chemical compound C(C1=CC=CC=C1)C1(CCC(CC1)NC(=O)C(CO)NC(O)=O)N1CCCCC1.C(C1=CC=CC=C1)OC(NC(C)C(NC1CCC(CC1)(C1=CC=CC=C1)N1CCOCC1)=O)=O FGJYIQSDGPUFKV-UHFFFAOYSA-N 0.000 claims description 2
- GDHCHHAFAPRDOA-UHFFFAOYSA-N CC(CC(C(NC1CCC(CC1)(N1CCCCC1)C1=CC=CC=C1)=O)NC(=O)CNC(O)=O)C.C(C1=CC=CC=C1)OC(NCCCCCC(NC1CCC(CC1)(CC1=CC=C(C=C1)C)N(C)C)=O)=O Chemical compound CC(CC(C(NC1CCC(CC1)(N1CCCCC1)C1=CC=CC=C1)=O)NC(=O)CNC(O)=O)C.C(C1=CC=CC=C1)OC(NCCCCCC(NC1CCC(CC1)(CC1=CC=C(C=C1)C)N(C)C)=O)=O GDHCHHAFAPRDOA-UHFFFAOYSA-N 0.000 claims description 2
- AWBCYFQLUYOOTH-UHFFFAOYSA-N [1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(C=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)C(NC(=O)O)CC1=CC=CC=C1 AWBCYFQLUYOOTH-UHFFFAOYSA-N 0.000 claims description 2
- NTBNZVUNMOBOGV-UHFFFAOYSA-N [1-[[4-(azepan-1-yl)-4-benzylcyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCCCCC2)CCC1NC(=O)C(NC(=O)O)CC1=CC=CC=C1 NTBNZVUNMOBOGV-UHFFFAOYSA-N 0.000 claims description 2
- ATIUKQFGTJTHKI-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(O)=O)CCC1(N(C)C)CC1=CC=CC=C1F ATIUKQFGTJTHKI-UHFFFAOYSA-N 0.000 claims description 2
- WAGCNQBAFBJYDW-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]amino]-3-methyl-1-oxobutan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(NC(O)=O)C(C)C)CCC1(N(C)C)CC1=CC=C(F)C=C1 WAGCNQBAFBJYDW-UHFFFAOYSA-N 0.000 claims description 2
- FAFDQGPPBAJJMT-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamic acid Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(NC(=O)C(CO)NC(O)=O)CC1 FAFDQGPPBAJJMT-UHFFFAOYSA-N 0.000 claims description 2
- MESWHKVGFYMHCX-UHFFFAOYSA-N [1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(O)=O)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 MESWHKVGFYMHCX-UHFFFAOYSA-N 0.000 claims description 2
- KCEBRBACQFUNQF-UHFFFAOYSA-N [1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamic acid Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)C(CO)NC(O)=O)CC1 KCEBRBACQFUNQF-UHFFFAOYSA-N 0.000 claims description 2
- UKEPNCBKOKGJNX-UHFFFAOYSA-N [1-oxo-3-phenyl-1-[(4-phenyl-4-piperidin-1-ylcyclohexyl)amino]propan-2-yl]carbamic acid Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(NC(=O)O)CC1=CC=CC=C1 UKEPNCBKOKGJNX-UHFFFAOYSA-N 0.000 claims description 2
- SHUDCDCVMCYRHB-UHFFFAOYSA-N [3-[[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]amino]-3-oxopropyl]carbamic acid Chemical compound C=1C=CC(F)=CC=1C1(N(C)C)CCC(NC(=O)CCNC(O)=O)CC1 SHUDCDCVMCYRHB-UHFFFAOYSA-N 0.000 claims description 2
- XMUDCZNTNLWMIO-UHFFFAOYSA-N [3-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-3-oxopropyl]carbamic acid Chemical compound C=1C=CC(F)=CC=1CC1(N(C)C)CCC(NC(=O)CCNC(O)=O)CC1 XMUDCZNTNLWMIO-UHFFFAOYSA-N 0.000 claims description 2
- IIYMGNJTKMIVKM-UHFFFAOYSA-N [3-hydroxy-1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxopropan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(NC(O)=O)CO)CCC1(C=1C=CC=CC=1)N1CCOCC1 IIYMGNJTKMIVKM-UHFFFAOYSA-N 0.000 claims description 2
- GALDRUCNMPBRIP-UHFFFAOYSA-N [5-amino-1-[(4-benzyl-4-piperidin-1-ylcyclohexyl)amino]-1,5-dioxopentan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(NC(O)=O)CCC(=O)N)CCC1(N1CCCCC1)CC1=CC=CC=C1 GALDRUCNMPBRIP-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001875 compounds Chemical class 0.000 description 24
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
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- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 8
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023508.2 | 2004-05-10 | ||
| DE102004023508A DE102004023508A1 (de) | 2004-05-10 | 2004-05-10 | Säurederivate substituierter Cyclohexyl-1,4-diamine |
| PCT/EP2005/004910 WO2005110973A1 (de) | 2004-05-10 | 2005-05-06 | Saürederivate substituierter cyclohexyl-1,4-diamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2566215A1 CA2566215A1 (en) | 2005-11-24 |
| CA2566215C true CA2566215C (en) | 2012-08-21 |
Family
ID=34967455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2566215A Expired - Fee Related CA2566215C (en) | 2004-05-10 | 2005-05-06 | Cyclohexyl-1,4-diamines substituted by acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7439394B2 (https=) |
| EP (1) | EP1751090B1 (https=) |
| JP (1) | JP5084498B2 (https=) |
| CA (1) | CA2566215C (https=) |
| DE (1) | DE102004023508A1 (https=) |
| WO (1) | WO2005110973A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200940523A (en) * | 2008-03-17 | 2009-10-01 | Gruenenthal Gmbh | Substituted sulfonamide derivatives |
| 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 |
| HK1199259A1 (en) | 2011-08-15 | 2015-06-26 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
| TW202547460A (zh) * | 2024-04-04 | 2025-12-16 | 日商橘生藥品工業股份有限公司 | 取代磺醯胺化合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
-
2004
- 2004-05-10 DE DE102004023508A patent/DE102004023508A1/de not_active Withdrawn
-
2005
- 2005-05-06 CA CA2566215A patent/CA2566215C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512030A patent/JP5084498B2/ja not_active Expired - Fee Related
- 2005-05-06 WO PCT/EP2005/004910 patent/WO2005110973A1/de not_active Ceased
- 2005-05-06 EP EP05741145.6A patent/EP1751090B1/de not_active Expired - Lifetime
-
2006
- 2006-11-09 US US11/594,944 patent/US7439394B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20070117803A1 (en) | 2007-05-24 |
| JP5084498B2 (ja) | 2012-11-28 |
| WO2005110973A1 (de) | 2005-11-24 |
| EP1751090A1 (de) | 2007-02-14 |
| US7439394B2 (en) | 2008-10-21 |
| JP2007536320A (ja) | 2007-12-13 |
| EP1751090B1 (de) | 2014-10-08 |
| DE102004023508A1 (de) | 2005-12-08 |
| CA2566215A1 (en) | 2005-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170510 |