ZA200507795B - 4-(4-Heterocyclylalkoxy)phenyl)-1-(heterocyclyl-carbonyl) piperidine derivatives and related compounds as histamine H3 antagonists for the treatment of neurological diseases such as Alzheimer's - Google Patents
4-(4-Heterocyclylalkoxy)phenyl)-1-(heterocyclyl-carbonyl) piperidine derivatives and related compounds as histamine H3 antagonists for the treatment of neurological diseases such as Alzheimer's Download PDFInfo
- Publication number
- ZA200507795B ZA200507795B ZA200507795A ZA200507795A ZA200507795B ZA 200507795 B ZA200507795 B ZA 200507795B ZA 200507795 A ZA200507795 A ZA 200507795A ZA 200507795 A ZA200507795 A ZA 200507795A ZA 200507795 B ZA200507795 B ZA 200507795B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- alkyl
- formula
- pharmaceutically acceptable
- piperidinyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 120
- 238000011282 treatment Methods 0.000 title claims description 18
- 208000012902 Nervous system disease Diseases 0.000 title claims description 7
- 208000025966 Neurological disease Diseases 0.000 title claims description 7
- 239000003395 histamine H3 receptor antagonist Substances 0.000 title description 3
- 150000003053 piperidines Chemical class 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- -1 cyano, amino Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 173
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
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- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 73
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- 238000003756 stirring Methods 0.000 description 23
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- 210000004027 cell Anatomy 0.000 description 17
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
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- 229920002223 polystyrene Polymers 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
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- OULQSDHKCOOGMJ-UHFFFAOYSA-N 1-[3-(4-piperidin-4-ylphenoxy)propyl]piperidine Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C1CCNCC1 OULQSDHKCOOGMJ-UHFFFAOYSA-N 0.000 description 5
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- QXBGAJNZGXEKJO-UHFFFAOYSA-N tert-butyl 4-hydroxy-4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidine-1-carboxylate Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2(O)CCN(CC2)C(=O)OC(C)(C)C)C=C1 QXBGAJNZGXEKJO-UHFFFAOYSA-N 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
- A61P25/16—Anti-Parkinson drugs
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- 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
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- 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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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
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| GBGB0308333.4A GB0308333D0 (en) | 2003-04-10 | 2003-04-10 | Novel compounds |
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Families Citing this family (28)
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| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| ES2371774T3 (es) * | 2005-06-03 | 2012-01-10 | Abbott Laboratories | Derivados de ciclobutilamina. |
| CA2609957A1 (en) | 2005-06-20 | 2007-01-04 | Schering Corporation | Carbon-linked substituted piperidines and derivatives thereof useful as histamine h3 antagonists |
| DE602006010870D1 (de) | 2005-06-20 | 2010-01-14 | Schering Corp | Als antagonisten von histamin h3 geeignete piperidinderivate |
| GB0514812D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| WO2007035703A1 (en) | 2005-09-20 | 2007-03-29 | Schering Corporation | 1- [ [1- [ (2-amin0-6-methyl-4-pyridinyl) methyl] -4-flu0r0-4-piperidinyl,] carbonyl] -4- [2- (2-pyridinyl) -3h-imidaz0 [4 , 5-b] pyridin-3-yl] piperidine useful as histamine h3 antagonist |
| US7943605B2 (en) | 2005-10-27 | 2011-05-17 | Ucb Pharma S.A. | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| PE20071068A1 (es) | 2005-12-20 | 2007-12-13 | Glaxo Group Ltd | Acido 3-(4-{[4-(4-{[3-(3,3-dimetil-1-piperidinil)propil]oxi}fenil)-1-piperidinil]carbonil}-1-naftalenil)propanoico o propenoico, sales de los mismos, como antagonistas de los receptores h1 y h3 |
| JP2009521448A (ja) | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用なフェノキシピペリジンおよびそのアナログ |
| AU2006331850A1 (en) | 2005-12-21 | 2007-07-05 | Schering Corporation | Substituted aniline derivatives useful as histamine H3 antagonists |
| EP2502918B1 (en) | 2006-07-25 | 2015-03-25 | Cephalon, Inc. | Pyridazinone Derivatives |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| KR101108109B1 (ko) * | 2007-01-22 | 2012-02-06 | 화이자 프로덕츠 인코포레이티드 | 치료 화합물의 토실레이트 염 및 이의 약학 조성물 |
| AU2008279447A1 (en) | 2007-07-19 | 2009-01-29 | Metabolex, Inc. | N-azacyclic substituted pyrrole, pyrazole, imidazole, triazole and tetrazole derivatives as agonists of the RUP3 or GPR119 receptor for the treatment of diabetes and metabolic disorders |
| BRPI0914891A2 (pt) * | 2008-06-20 | 2015-11-24 | Metabolex Inc | agonistas de aril gpr119 e usos dos mesmos |
| EP2483281B1 (en) | 2009-10-01 | 2014-06-04 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
| BR112012032248A2 (pt) | 2010-06-23 | 2016-09-13 | Metabolex Inc | composições de 5-etil-2-{4-[-4(-4-tetrazol-1-il-fenoximetil)-tiazol-2-il]-piperidin-1-il}-pirimidina |
| BR112014013461A2 (pt) | 2011-12-08 | 2017-06-13 | Taisho Pharmaceutical Co Ltd | derivado de fenilpirrol |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| HUP1300139A2 (en) * | 2013-03-06 | 2014-09-29 | Richter Gedeon Nyrt | Phenoxypiperidine h3 antagonists |
| JP6426694B2 (ja) | 2013-03-15 | 2018-11-21 | グローバル ブラッド セラピューティクス インコーポレイテッド | ヘモグロビンの修飾のための化合物及びその使用 |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| CN106715440B (zh) | 2015-04-21 | 2019-02-22 | 江苏恒瑞医药股份有限公司 | 咪唑并异吲哚类衍生物、其制备方法及其在医药上的应用 |
| WO2018026890A1 (en) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
| MX2021009685A (es) * | 2019-03-05 | 2021-09-10 | Eisai R&D Man Co Ltd | Compuesto heterociclo pentaciclico. |
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| US4166853A (en) * | 1978-05-05 | 1979-09-04 | The Upjohn Company | Antihypertensive 7-trifluoromethyl-4-aminoquinolones |
| JPH07509694A (ja) * | 1992-05-14 | 1995-10-26 | ベイラー・カレッジ・オブ・メディシン | 突然変異したステロイドホルモン受容体，その使用方法および遺伝子治療のための分子スイッチ |
| US5364791A (en) * | 1992-05-14 | 1994-11-15 | Elisabetta Vegeto | Progesterone receptor having C. terminal hormone binding domain truncations |
| DE4407139A1 (de) * | 1994-03-04 | 1995-09-07 | Thomae Gmbh Dr K | Aryl-1-azacycloalkane und deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
| CA2214288C (en) * | 1996-09-18 | 2006-07-18 | Lonza Ag | Process for the preparation of 1-acyl-4-arylpiperidines |
| EP0837065A1 (de) * | 1996-10-16 | 1998-04-22 | Ciba SC Holding AG | Phenylglycidylether-HALS |
| JP4516717B2 (ja) * | 2000-07-13 | 2010-08-04 | アボット・ラボラトリーズ | ヒスタミン−３受容体リガンドとしての１，３−二置換ピロリジン及び１，３，３−三置換ピロリジン並びにそれらの治療的応用 |
| US6515013B2 (en) * | 2000-07-13 | 2003-02-04 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| CA2418369A1 (en) * | 2000-08-08 | 2002-02-14 | Richard Apodaca | Non-imidazole aryloxyalkylamines as h3 receptor ligands |
| CA2439152C (en) * | 2001-02-28 | 2008-06-17 | Merck & Co., Inc. | Acylated piperidine derivatives as melanocortin-4 receptor agonists |
| WO2002076440A2 (en) * | 2001-03-23 | 2002-10-03 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease with piperidin derivates |
| US7459461B2 (en) * | 2001-10-19 | 2008-12-02 | Ortho-Mcneil Pharmaceutical, Inc. | Phosphonic acid compounds as inhibitors of serine proteases |
-
2003
- 2003-04-10 GB GBGB0308333.4A patent/GB0308333D0/en not_active Ceased
-
2004
- 2004-04-07 AR ARP040101188A patent/AR044006A1/es not_active Application Discontinuation
- 2004-04-08 AT AT04726514T patent/ATE365039T1/de not_active IP Right Cessation
- 2004-04-08 US US10/551,985 patent/US20060205774A1/en not_active Abandoned
- 2004-04-08 RU RU2005134006/04A patent/RU2005134006A/ru not_active Application Discontinuation
- 2004-04-08 BR BRPI0409110-8A patent/BRPI0409110A/pt not_active Application Discontinuation
- 2004-04-08 ES ES04726514T patent/ES2288681T3/es not_active Expired - Lifetime
- 2004-04-08 MX MXPA05010816A patent/MXPA05010816A/es not_active Application Discontinuation
- 2004-04-08 AU AU2004228949A patent/AU2004228949B2/en not_active Ceased
- 2004-04-08 DE DE602004007119T patent/DE602004007119T2/de not_active Expired - Fee Related
- 2004-04-08 CN CNA2004800161953A patent/CN1805747A/zh active Pending
- 2004-04-08 JP JP2006505136A patent/JP2006522771A/ja active Pending
- 2004-04-08 WO PCT/EP2004/003985 patent/WO2004089373A1/en not_active Ceased
- 2004-04-08 EP EP04726514A patent/EP1610786B9/en not_active Expired - Lifetime
- 2004-04-08 KR KR1020057019137A patent/KR20050111638A/ko not_active Withdrawn
- 2004-04-08 TW TW093109666A patent/TW200503710A/zh unknown
- 2004-04-08 CA CA002521899A patent/CA2521899A1/en not_active Abandoned
-
2005
- 2005-09-27 ZA ZA200507795A patent/ZA200507795B/en unknown
- 2005-10-06 CO CO05101708A patent/CO5640135A2/es not_active Application Discontinuation
- 2005-10-11 MA MA28548A patent/MA27726A1/fr unknown
- 2005-11-08 IS IS8118A patent/IS8118A/is unknown
- 2005-11-09 NO NO20055256A patent/NO20055256L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2521899A1 (en) | 2004-10-21 |
| MXPA05010816A (es) | 2005-12-05 |
| WO2004089373A1 (en) | 2004-10-21 |
| EP1610786B9 (en) | 2008-02-27 |
| BRPI0409110A (pt) | 2006-03-28 |
| CO5640135A2 (es) | 2006-05-31 |
| EP1610786B1 (en) | 2007-06-20 |
| CN1805747A (zh) | 2006-07-19 |
| DE602004007119D1 (de) | 2007-08-02 |
| NO20055256L (no) | 2006-01-10 |
| JP2006522771A (ja) | 2006-10-05 |
| ATE365039T1 (de) | 2007-07-15 |
| GB0308333D0 (en) | 2003-05-14 |
| ES2288681T3 (es) | 2008-01-16 |
| DE602004007119T2 (de) | 2008-02-21 |
| KR20050111638A (ko) | 2005-11-25 |
| RU2005134006A (ru) | 2006-04-10 |
| US20060205774A1 (en) | 2006-09-14 |
| NO20055256D0 (no) | 2005-11-09 |
| AR044006A1 (es) | 2005-08-24 |
| TW200503710A (en) | 2005-02-01 |
| EP1610786A1 (en) | 2006-01-04 |
| MA27726A1 (fr) | 2006-01-02 |
| AU2004228949A1 (en) | 2004-10-21 |
| AU2004228949B2 (en) | 2006-11-02 |
| IS8118A (is) | 2005-11-08 |
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