JP2005525333A - 置換縮合ピラゾールカルボン酸アリールアミド及び関連化合物 - Google Patents
置換縮合ピラゾールカルボン酸アリールアミド及び関連化合物 Download PDFInfo
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- JP2005525333A JP2005525333A JP2003566007A JP2003566007A JP2005525333A JP 2005525333 A JP2005525333 A JP 2005525333A JP 2003566007 A JP2003566007 A JP 2003566007A JP 2003566007 A JP2003566007 A JP 2003566007A JP 2005525333 A JP2005525333 A JP 2005525333A
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- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 298
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 title abstract description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 78
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 76
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 16
- 230000036506 anxiety Effects 0.000 claims abstract description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- RCTBACSGXPVNOF-UHFFFAOYSA-N 5,6,7,8-tetrahydropyrazolo[2,3]cyclohepta[2,4-b]pyridine-10-carboxylic acid Chemical compound C1CCC2=CC=CN=C2C2=C1NN=C2C(=O)O RCTBACSGXPVNOF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 250
- 229910052739 hydrogen Inorganic materials 0.000 claims description 240
- 239000001257 hydrogen Substances 0.000 claims description 240
- -1 cyano, nitro, amino Chemical group 0.000 claims description 136
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 130
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 129
- 229910052736 halogen Inorganic materials 0.000 claims description 96
- 150000002367 halogens Chemical class 0.000 claims description 95
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 72
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 229910052760 oxygen Inorganic materials 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 239000001301 oxygen Substances 0.000 claims description 45
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000002837 carbocyclic group Chemical group 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
- 125000006413 ring segment Chemical group 0.000 claims description 19
- 125000001544 thienyl group Chemical group 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 230000027455 binding Effects 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 210000004027 cell Anatomy 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- 208000019116 sleep disease Diseases 0.000 claims description 11
- 210000003169 central nervous system Anatomy 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 238000000338 in vitro Methods 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 210000001519 tissue Anatomy 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 238000005259 measurement Methods 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- 238000000211 autoradiogram Methods 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000002708 enhancing effect Effects 0.000 claims description 5
- MPSSQPWYDKLRTB-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindazole-3-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=NNC2=C1C(=O)CCC2 MPSSQPWYDKLRTB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 230000007781 signaling event Effects 0.000 claims description 5
- 239000006188 syrup Substances 0.000 claims description 5
- 235000020357 syrup Nutrition 0.000 claims description 5
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000000376 autoradiography Methods 0.000 claims description 4
- 230000007831 electrophysiology Effects 0.000 claims description 4
- 238000002001 electrophysiology Methods 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RCOONRVHELRGKW-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-1,4,5,6-tetrahydropyrazolo[3,4-e]indazole-8-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=NNC2=C1C1=NNC=C1CC2 RCOONRVHELRGKW-UHFFFAOYSA-N 0.000 claims description 3
- MEEPOBWLULRNOL-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-6,7-dihydro-5h-pyrazolo[3,4-h]quinazoline-9-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=NNC2=C1C1=NC=NC=C1CC2 MEEPOBWLULRNOL-UHFFFAOYSA-N 0.000 claims description 3
- FXDDFCGQANIZOT-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-6,7-dihydro-5h-pyrazolo[3,4-h]quinoline-9-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=NNC2=C1C1=NC=CC=C1CC2 FXDDFCGQANIZOT-UHFFFAOYSA-N 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 230000006403 short-term memory Effects 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 238000002372 labelling Methods 0.000 claims description 2
- INKQEZWTEKQNAN-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-2-methyl-6,7-dihydro-5h-pyrazolo[3,4-h]quinazoline-9-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=NNC2=C1C1=NC(C)=NC=C1CC2 INKQEZWTEKQNAN-UHFFFAOYSA-N 0.000 claims description 2
- FBAPDXMFBUMOBP-UHFFFAOYSA-N n-phenyl-5,6,7,8-tetrahydropyrazolo[2,3]cyclohepta[2,4-b]pyridine-10-carboxamide Chemical compound N=1NC=2CCCC3=CC=CN=C3C=2C=1C(=O)NC1=CC=CC=C1 FBAPDXMFBUMOBP-UHFFFAOYSA-N 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims 26
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
- 210000001124 body fluid Anatomy 0.000 claims 2
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- 210000004958 brain cell Anatomy 0.000 claims 1
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- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical group OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 230000004044 response Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 abstract description 24
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract description 18
- 239000000523 sample Substances 0.000 abstract description 16
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
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- YWTLNUUWJFOGPI-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[3,4-h]quinazoline-9-carboxylic acid Chemical compound C1CC2=CN=CN=C2C2=C1NN=C2C(=O)O YWTLNUUWJFOGPI-UHFFFAOYSA-N 0.000 abstract 1
- SSPQZSGBPQJKGU-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[3,4-h]quinoline-9-carboxylic acid Chemical compound C1CC2=CC=CN=C2C2=C1NN=C2C(=O)O SSPQZSGBPQJKGU-UHFFFAOYSA-N 0.000 abstract 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/20—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
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (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)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35531402P | 2002-02-07 | 2002-02-07 | |
| PCT/US2003/003872 WO2003066634A1 (en) | 2002-02-07 | 2003-02-07 | Substituted fused pyrazolecarboxylic acid arylamides and related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005525333A true JP2005525333A (ja) | 2005-08-25 |
| JP2005525333A5 JP2005525333A5 (https=) | 2006-04-06 |
Family
ID=27734501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003566007A Ceased JP2005525333A (ja) | 2002-02-07 | 2003-02-07 | 置換縮合ピラゾールカルボン酸アリールアミド及び関連化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6852730B2 (https=) |
| EP (1) | EP1472252A1 (https=) |
| JP (1) | JP2005525333A (https=) |
| AU (1) | AU2003212979A1 (https=) |
| BR (1) | BR0307504A (https=) |
| CA (1) | CA2486446A1 (https=) |
| MX (1) | MXPA04007606A (https=) |
| WO (1) | WO2003066634A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8513238B2 (en) | 2010-05-10 | 2013-08-20 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[E]azulenes |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| RU2015106013A (ru) * | 2012-08-10 | 2016-10-10 | Ф. Хоффманн-Ля Рош Аг | Соединения пиразолкарбоксамида, композиции и способы применения |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| TW202115024A (zh) | 2019-08-14 | 2021-04-16 | 美商英塞特公司 | 作為cdk2 抑制劑之咪唑基嘧啶基胺化合物 |
| AU2020364007A1 (en) | 2019-10-11 | 2022-04-28 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5750702A (en) * | 1993-10-27 | 1998-05-12 | Neurogen Corporation | Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands |
| US5484944A (en) * | 1993-10-27 | 1996-01-16 | Neurogen Corporation | Certain fused pyrrolecarboxanilides and their use as GABA brain receptor ligands |
| US5804686A (en) * | 1996-01-19 | 1998-09-08 | Neurogen Corporation | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
| US6211365B1 (en) * | 1996-01-19 | 2001-04-03 | Neurogen Corporation | Fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
| KR19990087585A (ko) * | 1996-03-08 | 1999-12-27 | 돈 리사 로얄 | 신경학적 활성제로서의 아졸로벤즈아제핀 유도체 |
| WO1997034870A1 (en) * | 1996-03-22 | 1997-09-25 | Neurogen Corporation | Certain fused pyrrolecarboxamides as gaba brain receptor ligands |
| US5723462A (en) * | 1996-04-26 | 1998-03-03 | Neurogen Corporation | Certain fused pyrrolecarboxamides a new class of GABA brain receptor ligands |
| IL135710A0 (en) | 1997-11-13 | 2001-05-20 | Pfizer Prod Inc | Method of synthesis of pyrrole amides |
| WO1999064425A1 (en) * | 1998-06-09 | 1999-12-16 | Neurogen Corporation | Substituted thienocycloalkylpyrazoles: dopamine receptor subtype specific ligands |
| GB9900222D0 (en) * | 1999-01-06 | 1999-02-24 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9911803D0 (en) | 1999-05-20 | 1999-07-21 | Merck Sharp & Dohme | Therapeutic combination |
| GB9911804D0 (en) | 1999-05-20 | 1999-07-21 | Merck Sharp & Dohme | Therapeutic combination |
| OA12015A (en) | 1999-08-31 | 2006-04-19 | Neurogen Corp | Fused pyrrolecarboxamides: gaba brain receptor ligands. |
| GB9929685D0 (en) * | 1999-12-15 | 2000-02-09 | Merck Sharp & Dohme | Therapeutic agents |
| MXPA03001186A (es) * | 2000-08-07 | 2004-04-20 | Neurogen Corp | Compuestos heterociclicos como ligandos del receptor acido gamma aminobutirico (gabaa). |
| BR0113697A (pt) | 2000-09-06 | 2003-07-22 | Neurogen Corp | Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, uso de um composto ou sal, embalagem e métodos para, para alterar a atividade transdutora de sinal dos receptores de gabaa, para tratar ansiedade, depressão, um distúrbio do sono, ou demência de alzheimer, para demonstrar a presença dos receptores de gabaa em células ou amostras de tecido e para preparar um composto |
| CA2419958A1 (en) | 2000-09-06 | 2002-03-14 | Neurogen Corporation | Substituted fused pyrroleimines and pyrazoleimines |
| EP1339681A1 (en) | 2000-12-04 | 2003-09-03 | Pfizer Products Inc. | Synthesis of fused pyrrolecarboxamides |
| US6861529B2 (en) | 2001-07-06 | 2005-03-01 | Pfizer Inc | Cycloalkypyrrole-3-carboxylic acid derivatives and heterocycloalkylpyrrole-3-carboxylic acid derivatives |
-
2003
- 2003-02-07 BR BR0307504-4A patent/BR0307504A/pt not_active Application Discontinuation
- 2003-02-07 WO PCT/US2003/003872 patent/WO2003066634A1/en not_active Ceased
- 2003-02-07 JP JP2003566007A patent/JP2005525333A/ja not_active Ceased
- 2003-02-07 EP EP03709023A patent/EP1472252A1/en not_active Withdrawn
- 2003-02-07 CA CA002486446A patent/CA2486446A1/en not_active Abandoned
- 2003-02-07 AU AU2003212979A patent/AU2003212979A1/en not_active Abandoned
- 2003-02-07 US US10/360,963 patent/US6852730B2/en not_active Expired - Fee Related
- 2003-02-07 MX MXPA04007606A patent/MXPA04007606A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BR0307504A (pt) | 2004-12-07 |
| WO2003066634A1 (en) | 2003-08-14 |
| EP1472252A1 (en) | 2004-11-03 |
| US6852730B2 (en) | 2005-02-08 |
| CA2486446A1 (en) | 2003-08-14 |
| AU2003212979A1 (en) | 2003-09-02 |
| MXPA04007606A (es) | 2004-11-10 |
| US20030216379A1 (en) | 2003-11-20 |
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