HRP20120108T2 - Spojevi benzoimidazol-karboksamida kao agonisti 5-ht4 receptora - Google Patents
Spojevi benzoimidazol-karboksamida kao agonisti 5-ht4 receptora Download PDFInfo
- Publication number
- HRP20120108T2 HRP20120108T2 HR20120108T HRP20120108T HRP20120108T2 HR P20120108 T2 HRP20120108 T2 HR P20120108T2 HR 20120108 T HR20120108 T HR 20120108T HR P20120108 T HRP20120108 T HR P20120108T HR P20120108 T2 HRP20120108 T2 HR P20120108T2
- Authority
- HR
- Croatia
- Prior art keywords
- piperidin
- ylmethyl
- phenyl
- carboxylic acid
- isopropyl
- Prior art date
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- XIZCDQOKKYYCRH-UHFFFAOYSA-N 1h-benzimidazole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=NC2=C1 XIZCDQOKKYYCRH-UHFFFAOYSA-N 0.000 title 1
- 108091005482 5-HT4 receptors Proteins 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 28
- 125000001424 substituent group Chemical group 0.000 claims abstract 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 12
- -1 amino furanyl Chemical group 0.000 claims abstract 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 9
- 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 abstract 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000012453 solvate Substances 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 238000000034 method Methods 0.000 claims 7
- 150000004702 methyl esters Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 206010010774 Constipation Diseases 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- MSVQYEFYBXIPIA-UHFFFAOYSA-N 4-[[4-[[(2-propan-2-yl-1h-benzimidazole-4-carbonyl)amino]methyl]piperidin-1-yl]methyl]piperidine-1-carboxylic acid Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC1CCN(C(O)=O)CC1 MSVQYEFYBXIPIA-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 206010021518 Impaired gastric emptying Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- MZOITCJKGUIQEI-UHFFFAOYSA-N methyl 4-[[4-[[(2-propan-2-yl-1h-benzimidazole-4-carbonyl)amino]methyl]piperidin-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1CN1CCC(CNC(=O)C=2C=3N=C(NC=3C=CC=2)C(C)C)CC1 MZOITCJKGUIQEI-UHFFFAOYSA-N 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- UGZNGVVJTSKSSH-UHFFFAOYSA-N 2-tert-butyl-n-[[1-[[1-(2-fluorobenzoyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=CC=C1F UGZNGVVJTSKSSH-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 201000006549 dyspepsia Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 210000000936 intestine Anatomy 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- CLATTZQKWOJCNH-UHFFFAOYSA-N methyl 4-[[4-[[(2-tert-butyl-1h-benzimidazole-4-carbonyl)amino]methyl]piperidin-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1CN1CCC(CNC(=O)C=2C=3N=C(NC=3C=CC=2)C(C)(C)C)CC1 CLATTZQKWOJCNH-UHFFFAOYSA-N 0.000 claims 2
- 230000004899 motility Effects 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- RKFFMBLKMOKZJA-UHFFFAOYSA-N 2-propan-2-yl-1h-benzimidazole-4-carboxylic acid Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(O)=O RKFFMBLKMOKZJA-UHFFFAOYSA-N 0.000 claims 1
- BBEHJUYJVPFQBD-UHFFFAOYSA-N 2-propan-2-yl-n-[[1-[[1-(thiophene-2-carbonyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=CS1 BBEHJUYJVPFQBD-UHFFFAOYSA-N 0.000 claims 1
- SENVEQQWYVBHPP-UHFFFAOYSA-N 2-tert-butyl-n-[[1-[[1-(3-methylbenzoyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-1h-benzimidazole-4-carboxamide Chemical compound CC1=CC=CC(C(=O)N2CCC(CN3CCC(CNC(=O)C=4C=5N=C(NC=5C=CC=4)C(C)(C)C)CC3)CC2)=C1 SENVEQQWYVBHPP-UHFFFAOYSA-N 0.000 claims 1
- SWGBXCFYKOCMGN-UHFFFAOYSA-N 2-tert-butyl-n-[[1-[[1-(4-fluorobenzoyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=C(F)C=C1 SWGBXCFYKOCMGN-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 206010051153 Diabetic gastroparesis Diseases 0.000 claims 1
- 206010054048 Postoperative ileus Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 208000001288 gastroparesis Diseases 0.000 claims 1
- 208000013617 idiopathic gastroparesis Diseases 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- CRPZGXDAOCLHPF-UHFFFAOYSA-N methyl 4-formylpiperidine-1-carboxylate Chemical compound COC(=O)N1CCC(C=O)CC1 CRPZGXDAOCLHPF-UHFFFAOYSA-N 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- ILIFRRWSQUFTDD-UHFFFAOYSA-N n-[[1-[[1-(2,4-difluorobenzoyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-2-propan-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=C(F)C=C1F ILIFRRWSQUFTDD-UHFFFAOYSA-N 0.000 claims 1
- CSTYAWWUQDXEGJ-UHFFFAOYSA-N n-[[1-[[1-(2-chlorobenzoyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-2-propan-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=CC=C1Cl CSTYAWWUQDXEGJ-UHFFFAOYSA-N 0.000 claims 1
- DLVGPWUJDKQEEF-UHFFFAOYSA-N n-[[1-[[1-(furan-2-carbonyl)piperidin-4-yl]methyl]piperidin-4-yl]methyl]-2-propan-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)C1=CC=CO1 DLVGPWUJDKQEEF-UHFFFAOYSA-N 0.000 claims 1
- CMEHTLJAUZYDDE-UHFFFAOYSA-N n-[[1-[[1-[(2-fluorophenyl)carbamoyl]piperidin-4-yl]methyl]piperidin-4-yl]methyl]-2-propan-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)NC1=CC=CC=C1F CMEHTLJAUZYDDE-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- FIRJNYGEYKBSHD-UHFFFAOYSA-N phenyl 4-[[4-[[(2-propan-2-yl-1h-benzimidazole-4-carbonyl)amino]methyl]piperidin-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1=CC=C2NC(C(C)C)=NC2=C1C(=O)NCC(CC1)CCN1CC(CC1)CCN1C(=O)OC1=CC=CC=C1 FIRJNYGEYKBSHD-UHFFFAOYSA-N 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 5
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D405/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
- G01N33/5058—Neurological cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Cell Biology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Toxicology (AREA)
- Microbiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Nutrition Science (AREA)
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- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68446605P | 2005-05-25 | 2005-05-25 | |
| US68447805P | 2005-05-25 | 2005-05-25 | |
| US74841505P | 2005-12-08 | 2005-12-08 | |
| PCT/US2006/020085 WO2006127815A2 (en) | 2005-05-25 | 2006-05-24 | Benzimidazole-carboxamide compounds as 5-ht4 receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20120108T1 HRP20120108T1 (en) | 2012-02-29 |
| HRP20120108T2 true HRP20120108T2 (hr) | 2012-03-31 |
Family
ID=37452788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120108T HRP20120108T2 (hr) | 2005-05-25 | 2012-02-01 | Spojevi benzoimidazol-karboksamida kao agonisti 5-ht4 receptora |
Country Status (27)
| Country | Link |
|---|---|
| US (10) | US8143279B2 (es) |
| EP (1) | EP1899324B1 (es) |
| JP (2) | JP5072111B2 (es) |
| KR (1) | KR101333280B1 (es) |
| AR (1) | AR057327A1 (es) |
| AT (1) | ATE535523T1 (es) |
| AU (1) | AU2006250009B2 (es) |
| BR (1) | BRPI0611202C1 (es) |
| CA (1) | CA2607280C (es) |
| CY (1) | CY1112366T1 (es) |
| DK (1) | DK1899324T3 (es) |
| EA (1) | EA013240B1 (es) |
| ES (1) | ES2376115T3 (es) |
| HK (1) | HK1110980A1 (es) |
| HR (1) | HRP20120108T2 (es) |
| IL (1) | IL186883A (es) |
| MA (1) | MA29541B1 (es) |
| MX (1) | MX2007014762A (es) |
| MY (1) | MY147756A (es) |
| NO (1) | NO339658B1 (es) |
| NZ (1) | NZ563068A (es) |
| PE (1) | PE20061446A1 (es) |
| PL (1) | PL1899324T3 (es) |
| PT (1) | PT1899324E (es) |
| SI (1) | SI1899324T1 (es) |
| TW (1) | TWI388555B (es) |
| WO (1) | WO2006127815A2 (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP2184A (en) * | 2003-09-03 | 2010-12-02 | Pfizer | Benzimidazolone compounds having 5-HT4 receptor agonistic activity. |
| US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
| MY147756A (en) | 2005-05-25 | 2013-01-15 | Theravance Inc | Benzimidazole-carboxamide compounds as 5-ht4 receptor agonists |
| US7256294B2 (en) * | 2005-05-25 | 2007-08-14 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| JP2012521428A (ja) * | 2009-03-23 | 2012-09-13 | メルク・シャープ・エンド・ドーム・コーポレイション | 疼痛治療用のｐ２ｘ３受容体アンタゴニスト |
| CN105832735A (zh) * | 2009-04-13 | 2016-08-10 | 施万生物制药研发Ip有限责任公司 | 用于治疗认知障碍的5-ht4受体促效剂化合物 |
| WO2011092293A2 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Cyclohexyl amide derivatives as crf receptor antagonists |
| US20120295942A1 (en) | 2010-02-01 | 2012-11-22 | Nicholas James Devereux | Pyrazolo[5,1b]oxazole Derivatives as CRF-1 Receptor Antagonists |
| CN102753527B (zh) | 2010-02-02 | 2014-12-24 | 诺华股份有限公司 | 用作crf受体拮抗剂的环己基酰胺衍生物 |
| KR20160040298A (ko) | 2013-08-09 | 2016-04-12 | 산텐 세이야꾸 가부시키가이샤 | 3,3-디메틸-3,4-디히드로-1h-퀴녹살린-2-온 유도체의 제조 방법 및 그 제조 방법의 중간체 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO984B1 (en) * | 1977-10-11 | 1979-12-01 | بيتشام غروب ليمتد | A dry pharmaceutical compound with a suitable dosage unit for oral administration |
| ES2109190B1 (es) | 1996-03-22 | 1998-07-01 | Univ Madrid Complutense | Nuevos derivados de bencimidazol con afinidad por los receptores serotoninergicos 5-ht /5-ht |
| JPH111472A (ja) | 1996-04-30 | 1999-01-06 | Dainippon Pharmaceut Co Ltd | ベンズアミド誘導体及びそれを含有する医薬組成物 |
| WO1999055674A1 (fr) | 1998-04-28 | 1999-11-04 | Dainippon Pharmaceutical Co., Ltd. | Derives de 1-[(1-substituee-4-piperidinyle)methyle]-4-piperidine, procede de production de ceux-ci, compositions medicinales contenant ces composes et intermediaires de ces composes |
| TR200200972T2 (tr) | 1998-11-03 | 2002-07-22 | Basf Aktiengesellschaft | İkameli 2-fenilbenzimidazoller, üretimleri ve kullanımları |
| US6353005B1 (en) * | 1999-03-02 | 2002-03-05 | Sepracor, Inc. | Method and compositions using (+) norcisapride in combination with proton pump inhibitors or H2 receptor antagonist |
| ES2154605B1 (es) | 1999-09-14 | 2001-11-16 | Univ Madrid Complutense | Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 |
| JP2001122784A (ja) | 1999-10-27 | 2001-05-08 | Dainippon Pharmaceut Co Ltd | １−［（１−置換−４−ピペリジニル）メチル］−４−ピペリジン誘導体からなる医薬 |
| AU7532601A (en) * | 2000-06-07 | 2001-12-17 | Aryx Therapeutics | Materials and methods for the treatment of gastroesophageal reflux disease |
| US6696468B2 (en) | 2002-05-16 | 2004-02-24 | Dainippon Pharmaceutical Co., Ltd. | (s)-4-amino-5-chloro-2-methoxy-n-[1-[1-(2-tetrahydrofuryl-carbonyl)-4-piperidinylmethyl]-4-piperidinyl]benzamide, process for the preparation thereof, pharmaceutical composition containing the same, and intermediate therefor |
| WO2004014895A1 (en) | 2002-08-05 | 2004-02-19 | Eli Lilly And Company | Piperazine substituted aryl benzodiazepines |
| CA2499494A1 (en) * | 2002-09-20 | 2004-04-01 | Pfizer Inc. | N-substituted piperidinyl-imidazopyridine compounds as 5-ht4 receptor modulators |
| JP2004277319A (ja) | 2003-03-14 | 2004-10-07 | Dainippon Pharmaceut Co Ltd | １−（４−ピペリジニルメチル）ピペリジニルアミド誘導体およびそれを含有する医薬組成物 |
| JP2004277320A (ja) | 2003-03-14 | 2004-10-07 | Dainippon Pharmaceut Co Ltd | １，４−ジ置換ピペリジン誘導体およびそれを含有する医薬組成物 |
| JP2004277318A (ja) | 2003-03-14 | 2004-10-07 | Dainippon Pharmaceut Co Ltd | １−（１−置換カルボニル−４−ピペリジニルメチル）ピペリジン誘導体およびそれを含有する医薬組成物 |
| AP2184A (en) | 2003-09-03 | 2010-12-02 | Pfizer | Benzimidazolone compounds having 5-HT4 receptor agonistic activity. |
| US7256294B2 (en) | 2005-05-25 | 2007-08-14 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
| MY147756A (en) * | 2005-05-25 | 2013-01-15 | Theravance Inc | Benzimidazole-carboxamide compounds as 5-ht4 receptor agonists |
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