JP2005525333A5 - - Google Patents
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- JP2005525333A5 JP2005525333A5 JP2003566007A JP2003566007A JP2005525333A5 JP 2005525333 A5 JP2005525333 A5 JP 2005525333A5 JP 2003566007 A JP2003566007 A JP 2003566007A JP 2003566007 A JP2003566007 A JP 2003566007A JP 2005525333 A5 JP2005525333 A5 JP 2005525333A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hydrogen
- cycloalkyl
- amino
- 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.)
- Ceased
Links
- 125000000217 alkyl group Chemical group 0.000 claims 69
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 63
- 150000001875 compounds Chemical class 0.000 claims 42
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- 239000001257 hydrogen Substances 0.000 claims 35
- 150000003839 salts Chemical class 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 26
- -1 cyano, nitro, amino Chemical group 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 102000005962 receptors Human genes 0.000 claims 12
- 108020003175 receptors Proteins 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 210000004027 cell Anatomy 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 238000000338 in vitro Methods 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 238000000211 autoradiogram Methods 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 3
- 230000007831 electrophysiology Effects 0.000 claims 3
- 238000002001 electrophysiology Methods 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 210000001124 body fluid Anatomy 0.000 claims 2
- 239000010839 body fluid Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 230000007781 signaling event Effects 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 210000001519 tissue Anatomy 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000000376 autoradiography Methods 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 210000004958 brain cell Anatomy 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 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
- 239000000499 gel Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- NTMRIZLYBYXRDQ-UHFFFAOYSA-N n-[1-[3-(azetidin-1-yl)propyl]pyrazol-3-yl]-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)NC(=N1)C=CN1CCCN1CCC1 NTMRIZLYBYXRDQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 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
- 230000019491 signal transduction Effects 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 0 CC(C*(C)*NC(c1n[n]c2c1-c1n[n](*)c(*)c1C(*)(*)*2)=O)*(*(C)*)=N Chemical compound CC(C*(C)*NC(c1n[n]c2c1-c1n[n](*)c(*)c1C(*)(*)*2)=O)*(*(C)*)=N 0.000 description 2
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 JP2005525333A (ja) | 2005-08-25 |
| JP2005525333A5 true 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 |
|---|---|---|---|---|
| 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
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