ZA200601324B - Benzimidazolone compounds having 5-HT4 receptor agonistic activity - Google Patents

Benzimidazolone compounds having 5-HT4 receptor agonistic activity Download PDF

Info

Publication number: ZA200601324B
Authority: ZA; South Africa
Prior art keywords: group; substituents; carbon atoms; substituted; independently selected
Prior art date: 2003-09-03

Application number

ZA200601324A

Other languages

English (en)

Inventor

Iguchi Satoru

Katsu Yasuhiro

Sone Hiroki

Uchida Chikara

Kojima Takashi

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

2003-09-03

Filing date

2006-02-14

Publication date

2007-05-30

2006-02-14 Application filed by Pfizer filed Critical Pfizer

2007-05-30 Publication of ZA200601324B publication Critical patent/ZA200601324B/en

Links

108091005482 5-HT4 receptors Proteins 0.000 title description 5
230000001270 agonistic effect Effects 0.000 title description 5
150000008641 benzimidazolones Chemical class 0.000 title description 5
125000001424 substituent group Chemical group 0.000 claims description 61
125000004432 carbon atom Chemical group C* 0.000 claims description 57
150000001875 compounds Chemical class 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 28
125000003277 amino group Chemical group 0.000 claims description 24
125000002947 alkylene group Chemical group 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 13
201000006549 dyspepsia Diseases 0.000 claims description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
108020003175 receptors Proteins 0.000 claims description 11
102000005962 receptors Human genes 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 8
208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
-1 hydroxytetrahydropyranyl Chemical group 0.000 claims description 7
230000001404 mediated effect Effects 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000024172 Cardiovascular disease Diseases 0.000 claims description 4
206010010774 Constipation Diseases 0.000 claims description 4
208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
206010019280 Heart failures Diseases 0.000 claims description 4
208000019695 Migraine disease Diseases 0.000 claims description 4
206010028813 Nausea Diseases 0.000 claims description 4
208000012902 Nervous system disease Diseases 0.000 claims description 4
208000025966 Neurological disease Diseases 0.000 claims description 4
206010030216 Oesophagitis Diseases 0.000 claims description 4
208000002193 Pain Diseases 0.000 claims description 4
206010047700 Vomiting Diseases 0.000 claims description 4
206010003119 arrhythmia Diseases 0.000 claims description 4
230000006793 arrhythmia Effects 0.000 claims description 4
208000015114 central nervous system disease Diseases 0.000 claims description 4
208000010877 cognitive disease Diseases 0.000 claims description 4
208000010643 digestive system disease Diseases 0.000 claims description 4
208000006881 esophagitis Diseases 0.000 claims description 4
230000030135 gastric motility Effects 0.000 claims description 4
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 4
208000018685 gastrointestinal system disease Diseases 0.000 claims description 4
206010027599 migraine Diseases 0.000 claims description 4
230000008693 nausea Effects 0.000 claims description 4
201000002859 sleep apnea Diseases 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims 3
239000013543 active substance Substances 0.000 claims 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
101001047090 Homo sapiens Potassium voltage-gated channel subfamily H member 2 Proteins 0.000 description 5
229940079593 drug Drugs 0.000 description 5
102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
238000000034 method Methods 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
239000002464 receptor antagonist Substances 0.000 description 3
229940044551 receptor antagonist Drugs 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
206010022998 Irritability Diseases 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
208000018452 Torsade de pointes Diseases 0.000 description 2
208000002363 Torsades de Pointes Diseases 0.000 description 2
239000000556 agonist Substances 0.000 description 2
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
230000008499 blood brain barrier function Effects 0.000 description 2
210000001218 blood-brain barrier Anatomy 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
229940000406 drug candidate Drugs 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
YPELFRMCRYSPKZ-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamide Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCN(CC=2C=CC(F)=CC=2)C1 YPELFRMCRYSPKZ-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
102000004257 Potassium Channel Human genes 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000036982 action potential Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 description 1
229960005132 cisapride Drugs 0.000 description 1
DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
229960002994 dofetilide Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000008406 drug-drug interaction Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000005714 functional activity Effects 0.000 description 1
208000029493 gastroesophageal disease Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229960004085 mosapride Drugs 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
229940125422 potassium channel blocker Drugs 0.000 description 1
239000003450 potassium channel blocker Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229960000351 terfenadine Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Classifications

- 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
- 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
- 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
- A61P1/04—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
- 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
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- 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
- 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
- A61P1/12—Antidiarrhoeals
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- 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
- A61P25/06—Antimigraine agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- 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
- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Ceramic Engineering (AREA)
Manufacturing & Machinery (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Materials Engineering (AREA)
Pain & Pain Management (AREA)
Structural Engineering (AREA)
Inorganic Chemistry (AREA)
Hospice & Palliative Care (AREA)
Endocrinology (AREA)
Nutrition Science (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Psychiatry (AREA)
Obesity (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200601324A 2003-09-03 2006-02-14 Benzimidazolone compounds having 5-HT4 receptor agonistic activity ZA200601324B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US50014403P	2003-09-03	2003-09-03

Publications (1)

Publication Number	Publication Date
ZA200601324B true ZA200601324B (en)	2007-05-30

Family

ID=34272920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200601324A ZA200601324B (en)	2003-09-03	2006-02-14	Benzimidazolone compounds having 5-HT4 receptor agonistic activity

Country Status (39)

Country	Link
US (2)	US7776885B2 (fr)
EP (1)	EP1664036B1 (fr)
JP (1)	JP3983269B1 (fr)
KR (1)	KR100738784B1 (fr)
CN (1)	CN100482659C (fr)
AP (1)	AP2184A (fr)
AR (1)	AR045552A1 (fr)
AT (1)	ATE539077T1 (fr)
AU (1)	AU2004268840B9 (fr)
BR (1)	BRPI0414105B8 (fr)
CA (1)	CA2537127C (fr)
CR (1)	CR8267A (fr)
CY (1)	CY1112321T1 (fr)
DK (1)	DK1664036T3 (fr)
EA (1)	EA009457B1 (fr)
EC (1)	ECSP066407A (fr)
ES (1)	ES2377484T3 (fr)
GE (1)	GEP20084527B (fr)
GT (1)	GT200400174A (fr)
HR (1)	HRP20120077T1 (fr)
IL (3)	IL173705A (fr)
IS (1)	IS8289A (fr)
MA (1)	MA28021A1 (fr)
MX (1)	MXPA06002550A (fr)
NL (1)	NL1026959C2 (fr)
NO (1)	NO20061519L (fr)
OA (1)	OA13248A (fr)
PA (1)	PA8610601A1 (fr)
PE (1)	PE20050874A1 (fr)
PL (1)	PL1664036T3 (fr)
PT (1)	PT1664036E (fr)
RS (1)	RS20060145A (fr)
SI (1)	SI1664036T1 (fr)
TN (1)	TNSN06073A1 (fr)
TW (1)	TW200510332A (fr)
UA (1)	UA86204C2 (fr)
UY (1)	UY28496A1 (fr)
WO (1)	WO2005021539A1 (fr)
ZA (1)	ZA200601324B (fr)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0934061B3 (fr)	1996-07-24	2015-01-21	Warner-Lambert Company LLC	Isobutylgaba et ses derives utilises pour le traitement de la douleur
GB0211230D0 (en)	2002-05-16	2002-06-26	Medinnova Sf	Treatment of heart failure
SE0301446D0 (sv)	2003-05-16	2003-05-16	Astrazeneca Ab	New Compounds
PL1664036T3 (pl) *	2003-09-03	2012-04-30	Pfizer	Związki benzimidazolonu wykazujące działanie agonistyczne względem receptora 5-ht4
TW200533348A (en)	2004-02-18	2005-10-16	Theravance Inc	Indazole-carboxamide compounds as 5-ht4 receptor agonists
US8309575B2 (en)	2004-04-07	2012-11-13	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
TWI351282B (en)	2004-04-07	2011-11-01	Theravance Inc	Quinolinone-carboxamide compounds as 5-ht4 recepto
US7728006B2 (en)	2004-04-07	2010-06-01	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US7737163B2 (en)	2004-06-15	2010-06-15	Pfizer Inc.	Benzimidazolone carboxylic acid derivatives
EA200801607A1 (ru)	2004-06-15	2008-10-30	Пфайзер Инк.	Производные бензимидазолонкарбоновой кислоты
DE602005014566D1 (de)	2004-11-05	2009-07-02	Theravance Inc	Chinolinon-carboxamid-verbindungen
DE602005016446D1 (de)	2004-11-05	2009-10-15	Theravance Inc	5-HT4-Rezeptoragonistenverbindungen
ATE469897T1 (de)	2004-12-22	2010-06-15	Theravance Inc	Indazolcarbonsäureamidverbindungen
AU2006217534B8 (en)	2005-02-22	2011-12-08	Pfizer Inc.	Oxyindole derivatives as 5HT4 receptor agonists
BRPI0608392A2 (pt)	2005-03-02	2009-12-29	Theravance Inc	compostos de quinolinona como agonistas do receptor 5-ht4
EP1861377B1 (fr) *	2005-03-15	2010-12-29	Pfizer, Inc.	Derives de benzimidazolone en tant que ligands de recepteur cb2
MY147756A (en)	2005-05-25	2013-01-15	Theravance Inc	Benzimidazole-carboxamide compounds as 5-ht4 receptor agonists
US7317022B2 (en) *	2005-06-07	2008-01-08	Theravance, Inc.	Benzoimidazolone-carboxamide compounds as 5-HT4 receptors agonists
EA016286B1 (ru) *	2005-09-30	2012-03-30	Глэксо Груп Лимитед	Соединения, которые обладают активностью по отношению к рецепторам м, и их применения в медицине
WO2007036711A1 (fr) *	2005-09-30	2007-04-05	Glaxo Group Limited	Benzimidazolones exerçant une activite au niveau du recepteur m1
EP1960389B1 (fr)	2005-09-30	2012-08-15	Glaxo Group Limited	Composes exerçant une activite au niveau du recepteur m1 et leurs utilisations en medecine
EP2314289A1 (fr) *	2005-10-31	2011-04-27	Braincells, Inc.	Modulation de la neurogenese dont la médiation est assurée par récepteur gaba
MY143574A (en) *	2005-11-22	2011-05-31	Theravance Inc	Carbamate compounds as 5-ht4 receptor agonists
GB0525068D0 (en)	2005-12-08	2006-01-18	Novartis Ag	Organic compounds
UY30048A1 (es) *	2005-12-23	2007-07-31	Astrazeneca Ab	Derivados sustituidos de la n,2-(1h-benzimidazol-1-il) acetamida, composiciones farmacéuticas conteniéndolos, procesos de preparación y aplicaciones
BRPI0707333B8 (pt) *	2006-01-24	2021-05-25	R Tech Ueno Ltd	composição farmacêutica que compreende um composto bicíclico, método de estabilização do composto bicíclico e formulação de cápsula de gelatina mole
TWI433839B (zh)	2006-08-11	2014-04-11	Neomed Inst	新穎的苯并咪唑衍生物290
US20080318964A1 (en) *	2007-06-19	2008-12-25	Protia, Llc	Deuterium-enriched eszopiclone
GB0718415D0 (en) *	2007-09-20	2007-10-31	Glaxo Group Ltd	Compounds
US8642772B2 (en)	2008-10-14	2014-02-04	Sk Biopharmaceuticals Co., Ltd.	Piperidine compounds, pharmaceutical composition comprising the same and its use
US8349852B2 (en)	2009-01-13	2013-01-08	Novartis Ag	Quinazolinone derivatives useful as vanilloid antagonists
US8232315B2 (en)	2009-06-26	2012-07-31	Sk Biopharmaceuticals Co., Ltd.	Methods for treating drug addiction and improving addiction-related behavior
ES2447295T3 (es)	2009-11-06	2014-03-11	Sk Biopharmaceuticals Co., Ltd.	Métodos para el tratamiento del trastorno de déficit de atención/hiperactividad
EP2496227B1 (fr)	2009-11-06	2019-05-22	SK Biopharmaceuticals Co., Ltd.	Procédés pour traiter un syndrome de fibromyalgie
CN102762572A (zh)	2010-02-01	2012-10-31	诺瓦提斯公司	作为CRF-1受体拮抗剂的吡唑并[5,1b]*唑衍生物
AR080056A1 (es)	2010-02-01	2012-03-07	Novartis Ag	Derivados de ciclohexil-amida como antagonistas de los receptores de crf
EP2531490B1 (fr)	2010-02-02	2014-10-15	Novartis AG	Dérivés de cyclohexylamide à titre d'antagonistes du récepteur crf
CN107260736A (zh) *	2010-02-12	2017-10-20	株式会社ＡｓｋＡｔ	用于治疗痴呆的5‑ht4受体激动剂
US9610274B2 (en)	2010-06-30	2017-04-04	Sk Biopharmaceuticals Co., Ltd.	Methods for treating bipolar disorder
US8623913B2 (en)	2010-06-30	2014-01-07	Sk Biopharmaceuticals Co., Ltd.	Methods for treating restless legs syndrome
WO2012074721A2 (fr) *	2010-12-02	2012-06-07	Lanco Biosciences, Inc.	Administration d'antagonistes des récepteurs de la sérotonine par des systèmes de micro-injection
UY34094A (es)	2011-05-27	2013-01-03	Novartis Ag	Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina
WO2013164790A1 (fr)	2012-05-03	2013-11-07	Novartis Ag	Sel de l-malate de dérivés de 2,7-diaza-spiro[4.5]déc-7-yle et ses formes cristallines à titre d'agonistes des récepteurs de ghreline
WO2017093890A1 (fr) *	2015-11-30	2017-06-08	Piramal Enterprises Limited	Formulation de comprimé à base de clobazam et son procédé de préparation
AR123872A1 (es) *	2020-10-23	2023-01-18	Hk Inno N Corp	Comprimido de desintegración oral, procedimiento de preparación del mismo, procedimiento para prevenir o tratar enfermedades y uso del mismo

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US63716A (en) *		1867-04-09		Improved cheery stoner
US3945953A (en) *	1972-04-21	1976-03-23	Ciba-Geigy Corporation	ω,ω'-Bis-[4-amino-3-aminomethyl-piperidyl-(1)]-alkanes, process for their manufacture and their use
CH566987A5 (fr) *	1972-04-21	1975-09-30	Ciba Geigy Ag
DE3336024A1 (de) *	1983-10-04	1985-04-18	Boehringer Ingelheim KG, 6507 Ingelheim	4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
US5223511A (en) *	1987-09-23	1993-06-29	Boehringer Ingelheim Italia S.P.A.	Benzimidazoline-2-oxo-1-carboxylic acid compounds useful as 5-HT receptor antagonists
KR0166088B1 (ko)	1990-01-23	1999-01-15	.	수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도
US5376645A (en)	1990-01-23	1994-12-27	University Of Kansas	Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
EP0522914A1 (fr) *	1991-06-27	1993-01-13	Synthelabo	Dérivés de 2-pipéridinylpyrimidine-4-carboxamide, leur préparation et leur application en thérapeutique
IT1251144B (it) *	1991-07-30	1995-05-04	Boehringer Ingelheim Italia	Derivati del benzimidazolone
GB9204565D0 (en)	1992-03-03	1992-04-15	Smithkline Beecham Plc	Pharmaceuticals
US5300512A (en)	1992-06-24	1994-04-05	G. D. Searle & Co.	Benzimidazole compounds
US5705498A (en) *	1992-11-05	1998-01-06	Smithkline Beecham Plc.	Piperidine derivatives as 5-HT4 receptor antagonists
TW252206B (fr) *	1993-09-01	1995-07-21	Philips Electronics Nv
IT1275903B1 (it) *	1995-03-14	1997-10-24	Boehringer Ingelheim Italia	Esteri e ammidi della 1,4-piperidina disostituita
GB9518953D0 (en) *	1995-09-15	1995-11-15	Pfizer Ltd	Pharmaceutical formulations
WO2000035298A1 (fr)	1996-11-27	2000-06-22	Wm. Wrigley Jr. Company	Chewing-gum contenant des agents medicamenteux actifs
GB9711643D0 (en)	1997-06-05	1997-07-30	Janssen Pharmaceutica Nv	Glass thermoplastic systems
WO1999012903A1 (fr)	1997-09-09	1999-03-18	Du Pont Pharmaceuticals Company	BENZIMIDAZOLINONES, BENZOXAZOLINONES, BENZOPIPERAZINONES, INDANONES ET LEURS DERIVES EN TANT QU'INHIBITEURS DU FACTEUR Xa
US6069152A (en) *	1997-10-07	2000-05-30	Eli Lilly And Company	5-HT4 agonists and antagonists
US6420410B1 (en) *	1998-11-24	2002-07-16	Cell Pathways, Inc.	Method for treating neoplasia by exposure to N,N′-substituted benzimidazol-2-ones
TW570920B (en) *	1998-12-22	2004-01-11	Janssen Pharmaceutica Nv	4-(aminomethyl)-piperidine benzamides for treating gastrointestinal disorders
WO2002053568A1 (fr) *	2000-12-28	2002-07-11	Mochida Pharmaceutical Co., Ltd.	Inhibiteurs de la biosynthese du cholesterol contenant comme principe actif des composes spiro tricycliques
SE0301446D0 (sv) *	2003-05-16	2003-05-16	Astrazeneca Ab	New Compounds
PL1664036T3 (pl) *	2003-09-03	2012-04-30	Pfizer	Związki benzimidazolonu wykazujące działanie agonistyczne względem receptora 5-ht4
US7737163B2 (en) *	2004-06-15	2010-06-15	Pfizer Inc.	Benzimidazolone carboxylic acid derivatives
EA200801607A1 (ru) *	2004-06-15	2008-10-30	Пфайзер Инк.	Производные бензимидазолонкарбоновой кислоты
MY147756A (en) *	2005-05-25	2013-01-15	Theravance Inc	Benzimidazole-carboxamide compounds as 5-ht4 receptor agonists

2004
- 2004-08-20 PL PL04744319T patent/PL1664036T3/pl unknown
- 2004-08-20 JP JP2006525197A patent/JP3983269B1/ja not_active Expired - Fee Related
- 2004-08-20 GE GEAP20049270A patent/GEP20084527B/en unknown
- 2004-08-20 CN CNB2004800252755A patent/CN100482659C/zh not_active Expired - Fee Related
- 2004-08-20 DK DK04744319.7T patent/DK1664036T3/da active
- 2004-08-20 AU AU2004268840A patent/AU2004268840B9/en not_active Ceased
- 2004-08-20 RS YUP-2006/0145A patent/RS20060145A/sr unknown
- 2004-08-20 UA UAA200602293A patent/UA86204C2/uk unknown
- 2004-08-20 EA EA200600327A patent/EA009457B1/ru not_active IP Right Cessation
- 2004-08-20 MX MXPA06002550A patent/MXPA06002550A/es active IP Right Grant
- 2004-08-20 AP AP2006003536A patent/AP2184A/xx active
- 2004-08-20 OA OA1200600069A patent/OA13248A/en unknown
- 2004-08-20 CA CA2537127A patent/CA2537127C/fr not_active Expired - Lifetime
- 2004-08-20 ES ES04744319T patent/ES2377484T3/es not_active Expired - Lifetime
- 2004-08-20 AT AT04744319T patent/ATE539077T1/de active
- 2004-08-20 SI SI200431820T patent/SI1664036T1/sl unknown
- 2004-08-20 KR KR1020067004335A patent/KR100738784B1/ko not_active Expired - Lifetime
- 2004-08-20 HR HR20120077T patent/HRP20120077T1/hr unknown
- 2004-08-20 EP EP04744319A patent/EP1664036B1/fr not_active Expired - Lifetime
- 2004-08-20 PT PT04744319T patent/PT1664036E/pt unknown
- 2004-08-20 WO PCT/IB2004/002741 patent/WO2005021539A1/fr not_active Ceased
- 2004-08-20 BR BRPI0414105A patent/BRPI0414105B8/pt not_active IP Right Cessation
- 2004-08-31 PE PE2004000831A patent/PE20050874A1/es not_active Application Discontinuation
- 2004-09-01 AR ARP040103133A patent/AR045552A1/es not_active Application Discontinuation
- 2004-09-02 PA PA20048610601A patent/PA8610601A1/es unknown
- 2004-09-02 GT GT200400174A patent/GT200400174A/es unknown
- 2004-09-02 UY UY28496A patent/UY28496A1/es not_active Application Discontinuation
- 2004-09-02 US US10/933,629 patent/US7776885B2/en active Active
- 2004-09-02 TW TW093126507A patent/TW200510332A/zh unknown
- 2004-09-03 NL NL1026959A patent/NL1026959C2/nl not_active IP Right Cessation
2006
- 2006-02-09 IS IS8289A patent/IS8289A/is unknown
- 2006-02-13 IL IL173705A patent/IL173705A/en not_active IP Right Cessation
- 2006-02-14 ZA ZA200601324A patent/ZA200601324B/en unknown
- 2006-03-02 CR CR8267A patent/CR8267A/es not_active Application Discontinuation
- 2006-03-03 EC EC2006006407A patent/ECSP066407A/es unknown
- 2006-03-03 MA MA28851A patent/MA28021A1/fr unknown
- 2006-03-03 TN TNP2006000073A patent/TNSN06073A1/en unknown
- 2006-04-03 NO NO20061519A patent/NO20061519L/no not_active Application Discontinuation
2010
- 2010-05-06 IL IL205600A patent/IL205600A0/en unknown
- 2010-05-06 IL IL205599A patent/IL205599A0/en unknown
- 2010-07-07 US US12/831,713 patent/US20100273794A1/en not_active Abandoned
2012
- 2012-02-06 CY CY20121100124T patent/CY1112321T1/el unknown

Also Published As

Publication number	Publication date
RS20060145A (sr)	2008-06-05
BRPI0414105B8 (pt)	2021-05-25
EA009457B1 (ru)	2007-12-28
ECSP066407A (es)	2006-09-18
TNSN06073A1 (en)	2007-10-03
AU2004268840B2 (en)	2010-09-23
GEP20084527B (en)	2008-11-10
NO20061519L (no)	2006-06-01
AU2004268840A1 (en)	2005-03-10
PT1664036E (pt)	2012-02-16
CN1845922A (zh)	2006-10-11
NL1026959C2 (nl)	2006-01-23
KR100738784B1 (ko)	2007-07-12
CA2537127A1 (fr)	2005-03-10
OA13248A (en)	2007-01-31
JP2007533613A (ja)	2007-11-22
US20100273794A1 (en)	2010-10-28
UA86204C2 (uk)	2009-04-10
MXPA06002550A (es)	2006-06-20
CR8267A (es)	2006-11-21
WO2005021539A1 (fr)	2005-03-10
EP1664036B1 (fr)	2011-12-28
IL205600A0 (en)	2010-11-30
NL1026959A1 (nl)	2005-03-07
GT200400174A (es)	2005-05-02
ES2377484T3 (es)	2012-03-28
CY1112321T1 (el)	2015-12-09
PA8610601A1 (es)	2005-03-28
AR045552A1 (es)	2005-11-02
BRPI0414105B1 (pt)	2018-08-14
KR20060087540A (ko)	2006-08-02
MA28021A1 (fr)	2006-07-03
PL1664036T3 (pl)	2012-04-30
TW200510332A (en)	2005-03-16
HRP20120077T1 (hr)	2012-02-29
US7776885B2 (en)	2010-08-17
AU2004268840B9 (en)	2011-02-03
PE20050874A1 (es)	2005-10-26
UY28496A1 (es)	2005-04-29
HK1093338A1 (zh)	2007-03-02
EA200600327A1 (ru)	2006-08-25
EP1664036A1 (fr)	2006-06-07
SI1664036T1 (sl)	2012-03-30
ATE539077T1 (de)	2012-01-15
AP2006003536A0 (en)	2006-04-30
BRPI0414105A (pt)	2006-11-21
IL173705A0 (en)	2006-07-05
IL173705A (en)	2013-04-30
IS8289A (is)	2006-02-09
DK1664036T3 (da)	2012-02-13
CA2537127C (fr)	2011-04-05
AP2184A (en)	2010-12-02
US20050148573A1 (en)	2005-07-07
JP3983269B1 (ja)	2007-09-26
CN100482659C (zh)	2009-04-29
IL205599A0 (en)	2010-11-30

Publication	Publication Date	Title
CA2537127A1 (fr)	2005-03-10	Composes de benzimidazolone a activite d'agonistes du recepteur 5-ht4
EP2051975B1 (fr)	2012-09-12	Prolinamides substitués, procédé de production et utilisation de ceux-ci comme médicaments
EP3265448B1 (fr)	2021-12-29	Promédicaments de riluzole et leur utilisation
JP6204484B2 (ja)	2017-09-27	キナーゼモジュレーターとして有用なヘテロアリール置換ピリジル化合物
CN100352437C (zh)	2007-12-05	哌嗪衍生物、它们的制备方法及其在制备治疗中枢神经系统(cns)疾病的药物中的应用
WO1999031073A1 (fr)	1999-06-24	Nouveaux derives de pyrimidine-5-carboxamide
WO2001021615A1 (fr)	2001-03-29	Dérivés de benzimidazole
JP2005511478A (ja)	2005-04-28	Ｎ−置換非アリール複素環アミジル系ｎｍｄａ／ｎｒ２ｂ拮抗薬
EA017919B1 (ru)	2013-04-30	Производные пиразин-2-карбоксамида для лечения заболеваний, которые поддаются лечению путем блокирования эпителиальных натриевых каналов
WO2007063925A1 (fr)	2007-06-07	Dérivé de 2-aminobenzamide
CA2545092A1 (fr)	2005-06-02	Composes d'acide quinolonecarboxylique a activite agoniste du recepteur 5-ht4
JP5067364B2 (ja)	2012-11-07	アシルアミノピペリジン化合物
JP2007055940A (ja)	2007-03-08	ピラゾロピリミジン誘導体
AU2009216149B2 (en)	2013-05-23	Amide derivative and pharmaceutical composition containing the same
EP1797076A1 (fr)	2007-06-20	Derives de benzimidazole, compositions les contenant et preparation et utilisation desdits derives
JP2007269629A (ja)	2007-10-18	キナゾリン誘導体
SK9398A3 (en)	1998-08-05	(r)-5-bromo-n-(1-ethyl-4-methylhexahydro-1h-1,4-diazepin-6-yl)-2- -methoxy-6-methylamino-3-pyridine-carboxamide, process for producing the same and medicinal composition containing the same
JP2004277318A (ja)	2004-10-07	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
KR20110080181A (ko)	2011-07-12	3-(벤질아미노)-피롤리딘 유도체 및 이의 ｎｋ-3 수용체 길항제로서의 용도
WO1999050262A1 (fr)	1999-10-07	Derives de pyridine inhibiteurs de pde iv
JP2004277319A (ja)	2004-10-07	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
HUP0402357A2 (hu)	2005-02-28	Antihisztaminok alkalmazása megnövelt koponyán belüli nyomás akut csökkentésére és gyógyszerkészítmények előállítására
JP2001122784A (ja)	2001-05-08	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
JP4559749B2 (ja)	2010-10-13	ピペラジニルピリジン誘導体
JP5156806B2 (ja)	2013-03-06	アミド誘導体からなる医薬