KR20070045263A - 카세인 키나제 Ｉε 억제제로서의 치환된 티에노피롤카복실산 아미드, 피롤로티아졸 카복실산 아미드 및 관련된유사체 - Google Patents
카세인 키나제 Ｉε 억제제로서의 치환된 티에노피롤카복실산 아미드, 피롤로티아졸 카복실산 아미드 및 관련된유사체 Download PDFInfo
- Publication number
- KR20070045263A KR20070045263A KR1020077003865A KR20077003865A KR20070045263A KR 20070045263 A KR20070045263 A KR 20070045263A KR 1020077003865 A KR1020077003865 A KR 1020077003865A KR 20077003865 A KR20077003865 A KR 20077003865A KR 20070045263 A KR20070045263 A KR 20070045263A
- Authority
- KR
- South Korea
- Prior art keywords
- carboxylic acid
- acid amide
- alkyl
- formula
- pyrrole
- 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
- 239000003112 inhibitor Substances 0.000 title abstract description 14
- 102000052052 Casein Kinase II Human genes 0.000 title abstract 2
- 108010010919 Casein Kinase II Proteins 0.000 title abstract 2
- SLPJGDQJLTYWCI-UHFFFAOYSA-N dimethyl-(4,5,6,7-tetrabromo-1h-benzoimidazol-2-yl)-amine Chemical compound BrC1=C(Br)C(Br)=C2NC(N(C)C)=NC2=C1Br SLPJGDQJLTYWCI-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001408 amides Chemical class 0.000 title description 18
- YRVMMDZANCTYNL-UHFFFAOYSA-N 2h-pyrrolo[2,3-d][1,3]thiazole-2-carboxamide Chemical class C1=NC2=NC(C(=O)N)SC2=C1 YRVMMDZANCTYNL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 238000000034 method Methods 0.000 claims abstract description 75
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- 108010031425 Casein Kinases Proteins 0.000 claims abstract description 25
- 208000019022 Mood disease Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 230000033764 rhythmic process Effects 0.000 claims description 37
- 230000007958 sleep Effects 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 21
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- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
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- FNWSTCZNXVPFRZ-UHFFFAOYSA-N 4-pyridin-2-ylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC=N1 FNWSTCZNXVPFRZ-UHFFFAOYSA-N 0.000 claims description 5
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- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
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- OICWBDMISQRIEM-UHFFFAOYSA-N 2,6-bis(phenylsulfanyl)-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound N=1C=2C(SC=3C=CC=CC=3)=C(C(=O)N)NC=2SC=1SC1=CC=CC=C1 OICWBDMISQRIEM-UHFFFAOYSA-N 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 claims description 4
- SVGBHSTYOGQVPE-UHFFFAOYSA-N 2,6-bis[(3-methoxyphenyl)sulfanyl]-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(SC=2SC=3NC(=C(SC=4C=C(OC)C=CC=4)C=3N=2)C(N)=O)=C1 SVGBHSTYOGQVPE-UHFFFAOYSA-N 0.000 claims description 2
- KHLCUPKDEHFRCJ-UHFFFAOYSA-N 2-methyl-6-[3-(trifluoromethoxy)phenyl]sulfanyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC(C)=NC=2C=1SC1=CC=CC(OC(F)(F)F)=C1 KHLCUPKDEHFRCJ-UHFFFAOYSA-N 0.000 claims description 2
- HJYHRWTZEFNDSI-UHFFFAOYSA-N 2-methyl-6-phenyl-4-sulfanylpyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound NC(=O)C=1N(S)C=2SC(C)=NC=2C=1C1=CC=CC=C1 HJYHRWTZEFNDSI-UHFFFAOYSA-N 0.000 claims description 2
- KARMTEAISSCLNV-UHFFFAOYSA-N 4-(2-methoxyphenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound COC1=CC=CC=C1SC1=C(C(N)=O)NC2=C1C=CS2 KARMTEAISSCLNV-UHFFFAOYSA-N 0.000 claims description 2
- LLODQNWTXWAEHQ-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC(Cl)=CC(Cl)=C1 LLODQNWTXWAEHQ-UHFFFAOYSA-N 0.000 claims description 2
- HOQJCJIERRLTCY-UHFFFAOYSA-N 4-(3-bromophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC(Br)=C1 HOQJCJIERRLTCY-UHFFFAOYSA-N 0.000 claims description 2
- GHMABAHOMNASAZ-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC(Cl)=C1 GHMABAHOMNASAZ-UHFFFAOYSA-N 0.000 claims description 2
- YKZLNVSFLNFVOY-UHFFFAOYSA-N 4-(3-methoxyphenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound COC1=CC=CC(SC=2C=3C=CSC=3NC=2C(N)=O)=C1 YKZLNVSFLNFVOY-UHFFFAOYSA-N 0.000 claims description 2
- UVOWKGFSUGZCGS-UHFFFAOYSA-N 4-(3-methylphenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound CC1=CC=CC(SC=2C=3C=CSC=3NC=2C(N)=O)=C1 UVOWKGFSUGZCGS-UHFFFAOYSA-N 0.000 claims description 2
- NTLRFOPPLIJBSC-UHFFFAOYSA-N 4-pyridin-4-ylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=NC=C1 NTLRFOPPLIJBSC-UHFFFAOYSA-N 0.000 claims description 2
- JYSYZRVJGHEJDK-UHFFFAOYSA-N 4-thiophen-2-ylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CS1 JYSYZRVJGHEJDK-UHFFFAOYSA-N 0.000 claims description 2
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- IAGGBMKLGCTCCG-UHFFFAOYSA-N 6-(2-aminophenyl)sulfanyl-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2C=CSC=2C=1SC1=CC=CC=C1N IAGGBMKLGCTCCG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
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- 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
- A61P25/24—Antidepressants
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
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- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
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| US60334704P | 2004-08-19 | 2004-08-19 | |
| US60/603,347 | 2004-08-19 |
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| KR20070045263A true KR20070045263A (ko) | 2007-05-02 |
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|---|---|
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| MY (1) | MY139831A (enExample) |
| PA (1) | PA8642801A1 (enExample) |
| PE (1) | PE20060630A1 (enExample) |
| PL (1) | PL1784409T3 (enExample) |
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| RS (1) | RS51413B (enExample) |
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| SI (1) | SI1784409T1 (enExample) |
| SV (1) | SV2006002190A (enExample) |
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| UY (1) | UY29077A1 (enExample) |
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| AU2004312530A1 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| US8053603B2 (en) | 2006-01-06 | 2011-11-08 | Sunovion Pharmaceuticals Inc. | Tetralone-based monoamine reuptake inhibitors |
| CA2636324C (en) | 2006-01-06 | 2012-03-20 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
| AU2007233041B2 (en) | 2006-03-31 | 2013-05-02 | Sepracor Inc. | Preparation of chiral amides and amines |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| EP1955699A1 (en) * | 2007-02-08 | 2008-08-13 | Boehringer Ingelheim Pharma GmbH & Co. KG | Use of flibanserin for the treatment of insomnia |
| JP5420534B2 (ja) | 2007-05-31 | 2014-02-19 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害薬としてのフェニル置換シクロアルキルアミン |
| EP2397481B1 (en) * | 2009-02-12 | 2014-03-12 | Pharmadesign, Inc. | Inhibitor of casein kinase 1delta and casein kinase 1epsilon |
| EP2435443B1 (en) * | 2009-05-28 | 2013-07-31 | Vertex Pharmaceuticals Incorporated | Aminopyrazole triazolothiadiazole inhibitors of c-met protien kinase |
| HRP20140252T1 (hr) * | 2009-10-28 | 2014-04-25 | Pfizer Inc. | Derivati imidazola kao inhibitori kazeinske kinaze |
| DE102009058280A1 (de) * | 2009-12-14 | 2011-06-16 | Merck Patent Gmbh | Thiazolderivate |
| RU2562833C2 (ru) | 2010-08-09 | 2015-09-10 | НБ Хелс Лаборатори Ко. Лтд. | Ингибитор казеинкиназы 1 дельта и казеинкиназы 1 е |
| CN109748927A (zh) * | 2017-11-03 | 2019-05-14 | 上海交通大学医学院附属瑞金医院 | 杂芳基酰胺类化合物、其制备方法、药用组合物及其应用 |
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| SE9702001D0 (sv) * | 1997-05-28 | 1997-05-28 | Astra Pharma Prod | Novel compounds |
| WO2000075669A1 (en) * | 1999-06-08 | 2000-12-14 | Aventis Pharmaceuticals Inc. | Screening methods for altering circadian rhythm proteins |
| AU2004303826A1 (en) * | 2003-12-11 | 2005-07-07 | Aventis Pharmaceuticals Inc. | Substituted 1H-pyrrolo[3,2-b, 3,2-c, and 2,3-c]pyridine-2-carboxamides and related analogs as inhibitors of casein kinase I Epsilon |
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2005
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- 2005-08-18 DE DE602005021889T patent/DE602005021889D1/de not_active Expired - Lifetime
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- 2005-08-18 PL PL05826812T patent/PL1784409T3/pl unknown
- 2005-08-18 EP EP05826812A patent/EP1784409B1/en not_active Expired - Lifetime
- 2005-08-18 MY MYPI20053879A patent/MY139831A/en unknown
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- 2005-08-18 JP JP2007528007A patent/JP4869232B2/ja not_active Expired - Fee Related
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- 2005-08-18 CN CNB2005800269958A patent/CN100562521C/zh not_active Expired - Fee Related
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2007
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2008
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2010
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Also Published As
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