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 PDF

Info

Publication number: ZA200507795B
Authority: ZA; South Africa
Prior art keywords: compound; alkyl; formula; pharmaceutically acceptable; piperidinyl
Prior art date: 2003-04-10

Application number

ZA200507795A

Other languages

English (en)

Inventor

Mark J Bamford

David K Dean

David M Wilson

Original Assignee

Glaxo Group Ltd

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.)

2003-04-10

Filing date

2005-09-27

Publication date

2006-07-26

2005-09-27 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2006-07-26 Publication of ZA200507795B publication Critical patent/ZA200507795B/en

Links

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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims description 2
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125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
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
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238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 73
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
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239000002904 solvent Substances 0.000 description 27
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238000003756 stirring Methods 0.000 description 23
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
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239000012267 brine Substances 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
239000004793 Polystyrene Substances 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
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239000012074 organic phase Substances 0.000 description 10
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
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235000011152 sodium sulphate Nutrition 0.000 description 9
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229920005989 resin Polymers 0.000 description 8
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
208000035475 disorder Diseases 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
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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
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
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
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
238000012950 reanalysis Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011808 rodent model Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
208000023516 stroke disease Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000002278 tabletting lubricant Substances 0.000 description 1
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
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
- 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
- A61P25/16—Anti-Parkinson drugs
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- 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)

ZA200507795A 2003-04-10 2005-09-27 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 ZA200507795B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0308333.4A GB0308333D0 (en)	2003-04-10	2003-04-10	Novel compounds

Publications (1)

Publication Number	Publication Date
ZA200507795B true ZA200507795B (en)	2006-07-26

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ID=9956580

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ZA200507795A ZA200507795B (en)	2003-04-10	2005-09-27	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

Country Status (22)

Country	Link
US (1)	US20060205774A1 (pt)
EP (1)	EP1610786B9 (pt)
JP (1)	JP2006522771A (pt)
KR (1)	KR20050111638A (pt)
CN (1)	CN1805747A (pt)
AR (1)	AR044006A1 (pt)
AT (1)	ATE365039T1 (pt)
AU (1)	AU2004228949B2 (pt)
BR (1)	BRPI0409110A (pt)
CA (1)	CA2521899A1 (pt)
CO (1)	CO5640135A2 (pt)
DE (1)	DE602004007119T2 (pt)
ES (1)	ES2288681T3 (pt)
GB (1)	GB0308333D0 (pt)
IS (1)	IS8118A (pt)
MA (1)	MA27726A1 (pt)
MX (1)	MXPA05010816A (pt)
NO (1)	NO20055256L (pt)
RU (1)	RU2005134006A (pt)
TW (1)	TW200503710A (pt)
WO (1)	WO2004089373A1 (pt)
ZA (1)	ZA200507795B (pt)

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JP2011524917A (ja) *	2008-06-20	2011-09-08	メタボレックス，インコーポレイテッド	アリールｇｐｒ１１９作動薬およびその使用
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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 EP EP04726514A patent/EP1610786B9/en not_active Expired - Lifetime
- 2004-04-08 BR BRPI0409110-8A patent/BRPI0409110A/pt not_active Application Discontinuation
- 2004-04-08 AU AU2004228949A patent/AU2004228949B2/en not_active Ceased
- 2004-04-08 KR KR1020057019137A patent/KR20050111638A/ko not_active Application Discontinuation
- 2004-04-08 WO PCT/EP2004/003985 patent/WO2004089373A1/en active IP Right Grant
- 2004-04-08 US US10/551,985 patent/US20060205774A1/en not_active Abandoned
- 2004-04-08 JP JP2006505136A patent/JP2006522771A/ja active Pending
- 2004-04-08 RU RU2005134006/04A patent/RU2005134006A/ru not_active Application Discontinuation
- 2004-04-08 TW TW093109666A patent/TW200503710A/zh unknown
- 2004-04-08 ES ES04726514T patent/ES2288681T3/es not_active Expired - Lifetime
- 2004-04-08 CA CA002521899A patent/CA2521899A1/en not_active Abandoned
- 2004-04-08 CN CNA2004800161953A patent/CN1805747A/zh active Pending
- 2004-04-08 AT AT04726514T patent/ATE365039T1/de not_active IP Right Cessation
- 2004-04-08 DE DE602004007119T patent/DE602004007119T2/de not_active Expired - Fee Related
- 2004-04-08 MX MXPA05010816A patent/MXPA05010816A/es not_active Application Discontinuation
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
AU2004228949B2 (en)	2006-11-02
TW200503710A (en)	2005-02-01
KR20050111638A (ko)	2005-11-25
IS8118A (is)	2005-11-08
ATE365039T1 (de)	2007-07-15
US20060205774A1 (en)	2006-09-14
CA2521899A1 (en)	2004-10-21
DE602004007119T2 (de)	2008-02-21
EP1610786B1 (en)	2007-06-20
EP1610786A1 (en)	2006-01-04
CO5640135A2 (es)	2006-05-31
RU2005134006A (ru)	2006-04-10
DE602004007119D1 (de)	2007-08-02
BRPI0409110A (pt)	2006-03-28
GB0308333D0 (en)	2003-05-14
AR044006A1 (es)	2005-08-24
NO20055256D0 (no)	2005-11-09
EP1610786B9 (en)	2008-02-27
JP2006522771A (ja)	2006-10-05
CN1805747A (zh)	2006-07-19
NO20055256L (no)	2006-01-10
MXPA05010816A (es)	2005-12-05
MA27726A1 (fr)	2006-01-02
WO2004089373A1 (en)	2004-10-21
ES2288681T3 (es)	2008-01-16
AU2004228949A1 (en)	2004-10-21

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