CA2649913A1 - N-benzoyl- and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists - Google Patents
N-benzoyl- and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists Download PDFInfo
- Publication number
- CA2649913A1 CA2649913A1 CA002649913A CA2649913A CA2649913A1 CA 2649913 A1 CA2649913 A1 CA 2649913A1 CA 002649913 A CA002649913 A CA 002649913A CA 2649913 A CA2649913 A CA 2649913A CA 2649913 A1 CA2649913 A1 CA 2649913A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethylamino
- phenyl
- pyrrolidin
- carbonyl
- benzoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000005557 antagonist Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 10
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
- -1 cycloheteroalkyl Chemical group 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 102000004384 Histamine H3 receptors Human genes 0.000 claims description 15
- 108090000981 Histamine H3 receptors Proteins 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- 208000010877 cognitive disease Diseases 0.000 claims description 12
- 102000005962 receptors Human genes 0.000 claims description 11
- 108020003175 receptors Proteins 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000012239 Developmental disease Diseases 0.000 claims description 3
- 208000020685 sleep-wake disease Diseases 0.000 claims description 3
- DMULPHWOFFXUNA-UHFFFAOYSA-N 3-chloro-n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C2=CC=CC=C2S1 DMULPHWOFFXUNA-UHFFFAOYSA-N 0.000 claims description 2
- RSYOMHXNWSBQSQ-UHFFFAOYSA-N 4-cyclohexyl-n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]benzamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=C(C2CCCCC2)C=C1 RSYOMHXNWSBQSQ-UHFFFAOYSA-N 0.000 claims description 2
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- XVMBEFQCSIKAQZ-IBGZPJMESA-N [(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]-(4-quinolin-4-yloxyphenyl)methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(OC=3C4=CC=CC=C4N=CC=3)=CC=2)CCCC1 XVMBEFQCSIKAQZ-IBGZPJMESA-N 0.000 claims description 2
- FAFBJBCVAFXQHO-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(isoquinolin-1-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC2=CC=CC=C12 FAFBJBCVAFXQHO-UHFFFAOYSA-N 0.000 claims description 2
- QEVDRWFDZMXCDJ-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(pyridin-2-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=CC=CC=N1 QEVDRWFDZMXCDJ-UHFFFAOYSA-N 0.000 claims description 2
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- MTYKYSGFMAMMOQ-SFHVURJKSA-N [4-(3-methoxyphenoxy)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC(OC=2C=CC(=CC=2)C(=O)N2C[C@H](CC2)N2CCCC2)=C1 MTYKYSGFMAMMOQ-SFHVURJKSA-N 0.000 claims description 2
- YBVCXYYJJQZRNW-IBGZPJMESA-N [4-(3-methylphenoxy)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound CC1=CC=CC(OC=2C=CC(=CC=2)C(=O)N2C[C@H](CC2)N2CCCC2)=C1 YBVCXYYJJQZRNW-IBGZPJMESA-N 0.000 claims description 2
- HHPVZMYBDRHDTL-SFHVURJKSA-N [4-(4-chlorophenoxy)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C(=O)N2C[C@H](CC2)N2CCCC2)C=C1 HHPVZMYBDRHDTL-SFHVURJKSA-N 0.000 claims description 2
- MOQGWEWITCELLN-SFHVURJKSA-N [4-(4-methoxyphenoxy)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(=O)N2C[C@H](CC2)N2CCCC2)C=C1 MOQGWEWITCELLN-SFHVURJKSA-N 0.000 claims description 2
- YBZTVABBMXYECK-IBGZPJMESA-N [4-(4-methylphenoxy)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C(=O)N2C[C@H](CC2)N2CCCC2)C=C1 YBZTVABBMXYECK-IBGZPJMESA-N 0.000 claims description 2
- RTRPSRRXGSCHKD-QFIPXVFZSA-N [4-[4-(4-fluorophenoxy)phenoxy]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(C(=O)N2C[C@H](CC2)N2CCCC2)C=C1 RTRPSRRXGSCHKD-QFIPXVFZSA-N 0.000 claims description 2
- 201000003723 learning disability Diseases 0.000 claims description 2
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- WHGUNHNLOVCEKY-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]-1-methylindole-2-carboxamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C WHGUNHNLOVCEKY-UHFFFAOYSA-N 0.000 claims description 2
- KLUDPWOLVUXGDO-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]-4-phenoxybenzamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 KLUDPWOLVUXGDO-UHFFFAOYSA-N 0.000 claims description 2
- ZZFHNRIQTHVXOO-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]-4-phenylbenzamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 ZZFHNRIQTHVXOO-UHFFFAOYSA-N 0.000 claims description 2
- UQZVCJSGSAIHPP-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]-7-methoxy-1-benzofuran-2-carboxamide Chemical compound O1C=2C(OC)=CC=CC=2C=C1C(=O)NC(C=C1)=CC=C1C(=O)N1CCC(N(C)C)C1 UQZVCJSGSAIHPP-UHFFFAOYSA-N 0.000 claims description 2
- WAQUETNOOMBFBP-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]quinoline-2-carboxamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=C(C=CC=C2)C2=N1 WAQUETNOOMBFBP-UHFFFAOYSA-N 0.000 claims description 2
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- SQKQXYJHTKDETF-SFHVURJKSA-N (4-phenoxyphenyl)-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)CCCC1 SQKQXYJHTKDETF-SFHVURJKSA-N 0.000 claims 2
- KWALJEGLEUQFMZ-UHFFFAOYSA-N 3-chloro-n-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]phenyl]thiophene-2-carboxamide Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CS1 KWALJEGLEUQFMZ-UHFFFAOYSA-N 0.000 claims 1
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- RNYXSJGBMGKIBA-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(1h-indol-5-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=CC=C(NC=C2)C2=C1 RNYXSJGBMGKIBA-UHFFFAOYSA-N 0.000 claims 1
- JQPUUYMBIYTUQT-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(7h-purin-6-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=NC2=C1N=CN2 JQPUUYMBIYTUQT-UHFFFAOYSA-N 0.000 claims 1
- APPDICQYWHQOBV-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(pyrimidin-2-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC=N1 APPDICQYWHQOBV-UHFFFAOYSA-N 0.000 claims 1
- AXAGRBLKRVZYNW-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(quinolin-5-ylamino)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=CC=CC2=NC=CC=C12 AXAGRBLKRVZYNW-UHFFFAOYSA-N 0.000 claims 1
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- GFSZGLWVDJWVLE-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(7-methylthieno[3,2-d]pyrimidin-4-yl)amino]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=NC2=C1SC=C2C GFSZGLWVDJWVLE-UHFFFAOYSA-N 0.000 claims 1
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- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P25/18—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80190506P | 2006-05-19 | 2006-05-19 | |
| US60/801,905 | 2006-05-19 | ||
| PCT/US2007/011765 WO2007136668A2 (en) | 2006-05-19 | 2007-05-16 | N-benzoyl-and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2649913A1 true CA2649913A1 (en) | 2007-11-29 |
Family
ID=38616614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002649913A Abandoned CA2649913A1 (en) | 2006-05-19 | 2007-05-16 | N-benzoyl- and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7842715B2 (https=) |
| EP (1) | EP2027086B1 (https=) |
| JP (1) | JP2009537542A (https=) |
| CN (1) | CN101432261A (https=) |
| AR (1) | AR061015A1 (https=) |
| AT (1) | ATE533744T1 (https=) |
| AU (1) | AU2007254232A1 (https=) |
| CA (1) | CA2649913A1 (https=) |
| MX (1) | MX2008014743A (https=) |
| PE (1) | PE20080371A1 (https=) |
| TW (1) | TW200811165A (https=) |
| WO (1) | WO2007136668A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1994022A2 (en) * | 2006-03-15 | 2008-11-26 | Wyeth a Corporation of the State of Delaware | N-substituted-azacyclylamines as histamine-3 antagonists |
| 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 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009097995A1 (de) * | 2008-02-07 | 2009-08-13 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8236792B2 (en) * | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| CN102186479A (zh) * | 2008-09-10 | 2011-09-14 | 凯利普西斯公司 | 用于治疗疾病的组胺受体的氨基嘧啶抑制剂 |
| WO2012059443A2 (en) * | 2010-11-01 | 2012-05-10 | Neurotune Ag | Novel neurotrypsin inhibitors |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| CN102784146A (zh) * | 2011-05-19 | 2012-11-21 | 复旦大学 | N-苯基喹唑啉-4-胺类衍生物的药用用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1416872A (en) * | 1972-03-10 | 1975-12-10 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
| US3933829A (en) * | 1974-08-22 | 1976-01-20 | John Wyeth & Brother Limited | 4-Aminoquinoline derivatives |
| US4166853A (en) * | 1978-05-05 | 1979-09-04 | The Upjohn Company | Antihypertensive 7-trifluoromethyl-4-aminoquinolones |
| US4159331A (en) * | 1978-05-05 | 1979-06-26 | The Upjohn Company | Antihypertensive 4-aminoquinolines |
| DK111387A (da) | 1986-03-05 | 1987-09-06 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, laegemiddel indeholdende saadanne derivater samt fremgangsmaade til fremstilling af derivaterne |
| US5656642A (en) | 1993-04-07 | 1997-08-12 | Otsuka Pharmaceutical Co., Ltd. | Peripheral vasodilating agent containing piperidine derivative as active ingredient |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US5747485A (en) * | 1995-04-13 | 1998-05-05 | Merck & Co., Inc. | Substituted azetidiones as anti-inflammatory and antidegenerative agents |
| TW531537B (en) | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
| ES2210747T3 (es) | 1997-05-01 | 2004-07-01 | Eli Lilly And Company | Agentes antitromboticos. |
| EP1009405A4 (en) | 1997-08-28 | 2001-05-09 | Merck & Co Inc | PAYRROLIDINE AND PIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY |
| SK285729B6 (sk) * | 1997-11-18 | 2007-07-06 | Teijin Pharma Limited | Zlúčenina derivátov cyklických amínov a jej použitie |
| EP1098892A1 (en) | 1998-07-20 | 2001-05-16 | MERCK PATENT GmbH | Biphenyl derivatives |
| AU2180500A (en) | 1998-12-15 | 2000-07-03 | Warner-Lambert Company | Use of a mek inhibitor for preventing transplant rejection |
| WO2001042224A1 (en) * | 1999-12-09 | 2001-06-14 | Mitsubishi Pharma Corporation | Carboxyamido derivatives |
| AU2001247906A1 (en) | 2000-03-31 | 2001-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Phenyl-substituted indoles and indazoles |
| JP2004520347A (ja) | 2001-01-15 | 2004-07-08 | グラクソ グループ リミテッド | Ｌｄｌ−受容体発現のインデューサーとしてのアリールピペリジンおよびピペラジン誘導体 |
| HN2002000156A (es) * | 2001-07-06 | 2003-11-27 | Inc Agouron Pharmaceuticals | Derivados de benzamida tiazol y composiciones farmaceuticas para inhibir la proliferacion de celulas y metodos para su utilización. |
| GB0120461D0 (en) | 2001-08-22 | 2001-10-17 | Astrazeneca Ab | Novel compounds |
| WO2003040402A2 (en) | 2001-11-09 | 2003-05-15 | The Regents Of The University Of California | Alpha-helix mimicry by a class of organic molecules |
| WO2003082272A1 (en) * | 2002-03-29 | 2003-10-09 | Chiron Corporation | Substituted benzazoles and use thereof as raf kinase inhibitors |
| JP4394959B2 (ja) | 2002-04-08 | 2010-01-06 | メルク エンド カムパニー インコーポレーテッド | Ａｋｔ活性の阻害剤 |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| WO2004052858A2 (en) | 2002-12-06 | 2004-06-24 | Eli Lilly And Company | Inhibitors of monoamine uptake |
| BRPI0408365B8 (pt) | 2003-03-14 | 2021-05-25 | Avidex Ltd | compostos heterocíclicos de imunomodulação |
| TW200505902A (en) * | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| AU2005243175B2 (en) * | 2004-05-14 | 2011-12-01 | Millennium Pharmaceuticals, Inc. | Compounds and methods for inhibiting mitotic progression by inhibition of Aurora kinase |
| TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
| US20060014733A1 (en) * | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
| CA2575081C (en) | 2004-07-26 | 2013-05-07 | Eli Lilly And Company | Oxazole derivatives as histamine h3 receptor agents, preparation and therapeutic uses |
| CN101006082B (zh) | 2004-08-23 | 2010-09-29 | 伊莱利利公司 | 组胺h3受体药剂、制备方法和治疗用途 |
| UY29149A1 (es) | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| US7381732B2 (en) * | 2004-10-26 | 2008-06-03 | Bristol-Myers Squibb Company | Pyrazolobenzamides and derivatives as factor Xa inhibitors |
| EP1848696A1 (en) * | 2005-01-21 | 2007-10-31 | Schering Corporation | Imidazole and benzimidazole derivates useful as histamine h3 antagonists |
| ES2426482T3 (es) | 2005-01-27 | 2013-10-23 | Kyowa Hakko Kirin Co., Ltd. | Inhibidor de IGF-1R |
| JP2008537953A (ja) * | 2005-04-15 | 2008-10-02 | エラン ファーマシューティカルズ，インコーポレイテッド | ブラジキニンｂ１受容体拮抗作用に有用な新規化合物 |
| EP1994022A2 (en) | 2006-03-15 | 2008-11-26 | Wyeth a Corporation of the State of Delaware | N-substituted-azacyclylamines as histamine-3 antagonists |
| CA2646585A1 (en) | 2006-03-20 | 2007-09-27 | Glaxo Group Limited | Compounds which potentiate ampa receptor and uses thereof in medicine |
| US20070238718A1 (en) | 2006-04-06 | 2007-10-11 | Matthias Grauert | Thiazolyl-dihydro-indazole |
| PE20081152A1 (es) | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
-
2007
- 2007-05-16 CN CNA2007800155388A patent/CN101432261A/zh active Pending
- 2007-05-16 JP JP2009511057A patent/JP2009537542A/ja not_active Withdrawn
- 2007-05-16 AT AT07777110T patent/ATE533744T1/de active
- 2007-05-16 EP EP07777110A patent/EP2027086B1/en not_active Not-in-force
- 2007-05-16 CA CA002649913A patent/CA2649913A1/en not_active Abandoned
- 2007-05-16 WO PCT/US2007/011765 patent/WO2007136668A2/en not_active Ceased
- 2007-05-16 PE PE2007000590A patent/PE20080371A1/es not_active Application Discontinuation
- 2007-05-16 AU AU2007254232A patent/AU2007254232A1/en not_active Abandoned
- 2007-05-16 MX MX2008014743A patent/MX2008014743A/es not_active Application Discontinuation
- 2007-05-17 TW TW096117605A patent/TW200811165A/zh unknown
- 2007-05-18 AR ARP070102147A patent/AR061015A1/es unknown
- 2007-05-18 US US11/804,686 patent/US7842715B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2027086A2 (en) | 2009-02-25 |
| EP2027086B1 (en) | 2011-11-16 |
| PE20080371A1 (es) | 2008-04-09 |
| US20070270440A1 (en) | 2007-11-22 |
| US7842715B2 (en) | 2010-11-30 |
| MX2008014743A (es) | 2008-12-01 |
| WO2007136668A2 (en) | 2007-11-29 |
| TW200811165A (en) | 2008-03-01 |
| WO2007136668A9 (en) | 2008-03-27 |
| WO2007136668A3 (en) | 2008-01-24 |
| ATE533744T1 (de) | 2011-12-15 |
| AU2007254232A1 (en) | 2007-11-29 |
| CN101432261A (zh) | 2009-05-13 |
| JP2009537542A (ja) | 2009-10-29 |
| AR061015A1 (es) | 2008-07-30 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20130516 |