CA2542077A1 - Pyrovalerone analogs and therapeutic uses thereof - Google Patents
Pyrovalerone analogs and therapeutic uses thereof Download PDFInfo
- Publication number
- CA2542077A1 CA2542077A1 CA002542077A CA2542077A CA2542077A1 CA 2542077 A1 CA2542077 A1 CA 2542077A1 CA 002542077 A CA002542077 A CA 002542077A CA 2542077 A CA2542077 A CA 2542077A CA 2542077 A1 CA2542077 A1 CA 2542077A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- mammal
- phenyl
- pentan
- substituted
- 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
- SWUVZKWCOBGPTH-UHFFFAOYSA-N pyrovalerone Chemical class C=1C=C(C)C=CC=1C(=O)C(CCC)N1CCCC1 SWUVZKWCOBGPTH-UHFFFAOYSA-N 0.000 title claims description 16
- 230000001225 therapeutic effect Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 67
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 67
- 101710164184 Synaptic vesicular amine transporter Proteins 0.000 claims abstract description 28
- 102100034333 Synaptic vesicular amine transporter Human genes 0.000 claims abstract description 28
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 23
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 23
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 17
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims description 100
- 241000124008 Mammalia Species 0.000 claims description 58
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 229910052801 chlorine Inorganic materials 0.000 claims description 43
- 230000004064 dysfunction Effects 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000002401 inhibitory effect Effects 0.000 claims description 30
- 229960003638 dopamine Drugs 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 230000004770 neurodegeneration Effects 0.000 claims description 15
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- -1 1 -Naphthalen-2-yl-2-pyrrolidin-1 -yl-pentan-1-one 2-Pyrrolidin-1-yl-1-m-tolyl-pentan-1-one 2-Pyrrolidin-1-yl-1-o-tolyl-pentan-1-one 2-Pyrrolidin-1-yl-1-(4-thiophen-2-yl-phenyl)-pentan-1-one Chemical compound 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229950010600 pyrovalerone Drugs 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
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- XCHIECWEKDGHNL-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(O)C=CC=1C(=O)C(CCC)N1CCCC1 XCHIECWEKDGHNL-UHFFFAOYSA-N 0.000 claims description 5
- HWYVHRCKBXGZLV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(OC)C=CC=1C(=O)C(CCC)N1CCCC1 HWYVHRCKBXGZLV-UHFFFAOYSA-N 0.000 claims description 5
- 230000000966 norepinephrine reuptake Effects 0.000 claims description 5
- HHSYAWUBPBEDMP-UHFFFAOYSA-N 1-(3-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=CC(C)=CC=1C(=O)C(CCC)N1CCCC1 HHSYAWUBPBEDMP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- KKTUFJIEHNEGDF-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(O)C(O)=CC=1C(=O)C(CCC)N1CCCC1 KKTUFJIEHNEGDF-UHFFFAOYSA-N 0.000 claims description 3
- WXZXQKCLNSPXHL-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyrrolidin-1-ylhexan-1-one Chemical compound C=1C=C(OC)C=CC=1C(=O)C(CCCC)N1CCCC1 WXZXQKCLNSPXHL-UHFFFAOYSA-N 0.000 claims description 3
- DLRWKNLMJAIFQB-UHFFFAOYSA-N 1-phenyl-2-pyrrolidin-1-ylheptan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(CCCCC)N1CCCC1 DLRWKNLMJAIFQB-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- SLPVYNPNJIYANF-UHFFFAOYSA-N 3-methyl-1-phenyl-2-pyrrolidin-1-ylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C(C)C)N1CCCC1 SLPVYNPNJIYANF-UHFFFAOYSA-N 0.000 claims description 3
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- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- GSESDIFGJCCBHN-UHFFFAOYSA-N α-pyrrolidinobutiophenone Chemical compound C=1C=CC=CC=1C(=O)C(CC)N1CCCC1 GSESDIFGJCCBHN-UHFFFAOYSA-N 0.000 claims description 3
- YDIIDRWHPFMLGR-UHFFFAOYSA-N α-pyrrolidinopentiophenone Chemical compound C=1C=CC=CC=1C(=O)C(CCC)N1CCCC1 YDIIDRWHPFMLGR-UHFFFAOYSA-N 0.000 claims description 3
- SWUVZKWCOBGPTH-OAHLLOKOSA-N (2r)-1-(4-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound N1([C@H](CCC)C(=O)C=2C=CC(C)=CC=2)CCCC1 SWUVZKWCOBGPTH-OAHLLOKOSA-N 0.000 claims description 2
- OVEGFFRUJIZDSI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-piperidin-1-ylpentan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C(CCC)N1CCCCC1 OVEGFFRUJIZDSI-UHFFFAOYSA-N 0.000 claims description 2
- DZULEPZTNHLZTO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-pyrrolidin-1-ylbutan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C(CC)N1CCCC1 DZULEPZTNHLZTO-UHFFFAOYSA-N 0.000 claims description 2
- SIFVHGKZPNIKBO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-pyrrolidin-1-ylpent-4-en-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C(CC=C)N1CCCC1 SIFVHGKZPNIKBO-UHFFFAOYSA-N 0.000 claims description 2
- NIGBFBTVONRYQN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(CCC)N1CCCC1 NIGBFBTVONRYQN-UHFFFAOYSA-N 0.000 claims description 2
- JREHJCKVQXOMFL-UHFFFAOYSA-N 1-(4-methylphenyl)-2-pyrrolidin-1-ylpent-4-en-1-one Chemical compound C1=CC(C)=CC=C1C(=O)C(CC=C)N1CCCC1 JREHJCKVQXOMFL-UHFFFAOYSA-N 0.000 claims description 2
- RYJXAZXFWIWTOJ-UHFFFAOYSA-N 1-phenyl-2-pyrrolidin-1-ylnonan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(CCCCCCC)N1CCCC1 RYJXAZXFWIWTOJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
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- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
- 230000001722 neurochemical effect Effects 0.000 claims 2
- 101100324465 Caenorhabditis elegans arr-1 gene Proteins 0.000 claims 1
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- 208000026139 Memory disease Diseases 0.000 claims 1
- BFZRWQXNOPQJEK-UHFFFAOYSA-N N1(CCCC1)C(C(=O)C1=CC=C(C=C1)OC)CCC.N1(CCCC1)C(C(=O)C1=CC=C(C=C1)O)CCC.N1(CCCC1)C(C(=O)C1=CC=C(C=C1)Br)CCC Chemical compound N1(CCCC1)C(C(=O)C1=CC=C(C=C1)OC)CCC.N1(CCCC1)C(C(=O)C1=CC=C(C=C1)O)CCC.N1(CCCC1)C(C(=O)C1=CC=C(C=C1)Br)CCC BFZRWQXNOPQJEK-UHFFFAOYSA-N 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 77
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- 208000013403 hyperactivity Diseases 0.000 description 1
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- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
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- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
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- IATJTXRWQPLRPJ-UHFFFAOYSA-N methyl 4-(2-bromopentanoyl)benzoate Chemical compound CCCC(Br)C(=O)C1=CC=C(C(=O)OC)C=C1 IATJTXRWQPLRPJ-UHFFFAOYSA-N 0.000 description 1
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- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
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- 238000012636 positron electron tomography Methods 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- 238000003569 transporter assay Methods 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- 238000011277 treatment modality Methods 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- DINAKCGOEKXDTP-UHFFFAOYSA-N tributyl-(1-methylpyrrol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN1C DINAKCGOEKXDTP-UHFFFAOYSA-N 0.000 description 1
- 150000003813 tropane derivatives Chemical class 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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- 238000010626 work up procedure Methods 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- A61P25/14—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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50988203P | 2003-10-08 | 2003-10-08 | |
| US60/509,882 | 2003-10-08 | ||
| PCT/US2004/033349 WO2005034878A2 (en) | 2003-10-08 | 2004-10-08 | Pyrovalerone analogs and therapeutic uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2542077A1 true CA2542077A1 (en) | 2005-04-21 |
Family
ID=34435034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002542077A Abandoned CA2542077A1 (en) | 2003-10-08 | 2004-10-08 | Pyrovalerone analogs and therapeutic uses thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20080234498A1 (https=) |
| EP (1) | EP1670755A4 (https=) |
| JP (1) | JP2007508314A (https=) |
| AU (1) | AU2004280256A1 (https=) |
| CA (1) | CA2542077A1 (https=) |
| WO (1) | WO2005034878A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI499414B (zh) | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| WO2008109591A1 (en) | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| UA117095C2 (uk) | 2011-12-22 | 2018-06-25 | Аліос Біофарма, Інк. | Нуклеозидна сполука або її фармацевтично прийнятна сіль |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| SG11201407336PA (en) | 2012-05-25 | 2015-03-30 | Janssen Sciences Ireland Uc | Uracyl spirooxetane nucleosides |
| GEP201706757B (en) | 2012-12-21 | 2017-10-25 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| GB2530783A (en) * | 2014-10-02 | 2016-04-06 | Randox Lab Ltd | Improved immunoassay for pyrrolidinophenones |
| AU2020256166A1 (en) | 2019-04-02 | 2021-10-14 | Aligos Therapeutics, Inc. | Compounds targeting PRMT5 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314970A (en) * | 1967-04-18 | Pykrolidino ketones | ||
| US3287217A (en) * | 1966-11-22 | Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure | ||
| US2369611A (en) * | 1938-12-24 | 1945-02-13 | Scheuing Georg | Analgetically effective tetrahydronaphthalene piperidyl derivatives |
| DE1161274B (de) * | 1960-04-07 | 1964-01-16 | Thomae Gmbh Dr K | Verfahren zur Herstellung von ª‡-Pyrrolidinoketonen und deren Salzen |
| CH395998A (de) * | 1961-05-05 | 1965-07-31 | Wander Ag Dr A | Verfahren zur Herstellung von a-Pyrrolidino-valerophenonen |
| FR2319332A1 (fr) * | 1975-07-28 | 1977-02-25 | Roussel Uclaf | Nouveaux derives de l'aminobenzocycloheptene et leurs sels, procede de preparation et application a titre de medicaments desdits produits |
| HU222726B1 (hu) * | 1990-02-06 | 2003-09-29 | Pfizer, Inc., | Piperidinszármazékok, eljárás elżállításukra és az ezeket tartalmazó gyógyszerkészítmények |
| JPH051033A (ja) * | 1991-06-18 | 1993-01-08 | Tanabe Seiyaku Co Ltd | ベンゾシクロヘプテン誘導体及びその製法 |
-
2004
- 2004-10-08 JP JP2006534415A patent/JP2007508314A/ja not_active Withdrawn
- 2004-10-08 AU AU2004280256A patent/AU2004280256A1/en not_active Abandoned
- 2004-10-08 WO PCT/US2004/033349 patent/WO2005034878A2/en not_active Ceased
- 2004-10-08 US US10/575,177 patent/US20080234498A1/en not_active Abandoned
- 2004-10-08 EP EP04809902A patent/EP1670755A4/en not_active Withdrawn
- 2004-10-08 CA CA002542077A patent/CA2542077A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080234498A1 (en) | 2008-09-25 |
| AU2004280256A1 (en) | 2005-04-21 |
| EP1670755A4 (en) | 2007-02-28 |
| JP2007508314A (ja) | 2007-04-05 |
| WO2005034878A2 (en) | 2005-04-21 |
| WO2005034878A3 (en) | 2005-06-30 |
| EP1670755A2 (en) | 2006-06-21 |
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