JP4465188B2 - 新規な化合物 - Google Patents
新規な化合物 Download PDFInfo
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- JP4465188B2 JP4465188B2 JP2003554090A JP2003554090A JP4465188B2 JP 4465188 B2 JP4465188 B2 JP 4465188B2 JP 2003554090 A JP2003554090 A JP 2003554090A JP 2003554090 A JP2003554090 A JP 2003554090A JP 4465188 B2 JP4465188 B2 JP 4465188B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 13
- -1 2-methoxyethoxy Chemical group 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- JXIMQRCXMARPHT-UHFFFAOYSA-N 3-[6-[2-(2-methoxyethoxy)ethoxy]isoquinolin-1-yl]-2-oxo-1,3-dihydroindole-5-carbonitrile;2,2,2-trifluoroacetic acid Chemical group OC(=O)C(F)(F)F.O=C1NC2=CC=C(C#N)C=C2C1C1=NC=CC2=CC(OCCOCCOC)=CC=C21 JXIMQRCXMARPHT-UHFFFAOYSA-N 0.000 claims description 3
- WLLRPFPHVRJYBG-UHFFFAOYSA-N 3-[6-(2-methoxyethoxy)isoquinolin-1-yl]-2-oxo-1,3-dihydroindole-5-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C1C1=NC=CC2=CC(OCCOC)=CC=C21 WLLRPFPHVRJYBG-UHFFFAOYSA-N 0.000 claims description 2
- ULSGICPPPXWHNK-UHFFFAOYSA-N 3-[6-[2-(2-methoxyethoxy)ethoxy]isoquinolin-1-yl]-2-oxo-1,3-dihydroindole-5-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C1C1=NC=CC2=CC(OCCOCCOC)=CC=C21 ULSGICPPPXWHNK-UHFFFAOYSA-N 0.000 claims description 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 abstract description 34
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- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 102000001267 GSK3 Human genes 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- 125000003545 alkoxy group Chemical group 0.000 description 36
- 229910052739 hydrogen Inorganic materials 0.000 description 36
- 239000001257 hydrogen Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
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- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 33
- 229910052760 oxygen Inorganic materials 0.000 description 32
- 229910052717 sulfur Inorganic materials 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 150000002431 hydrogen Chemical class 0.000 description 25
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 125000005843 halogen group Chemical group 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000005842 heteroatom Chemical group 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 14
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
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- 125000003072 pyrazolidinyl group Chemical group 0.000 description 7
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- 102000015735 Beta-catenin Human genes 0.000 description 6
- 108060000903 Beta-catenin Proteins 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 208000010877 cognitive disease Diseases 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 108010001483 Glycogen Synthase Proteins 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 108010026424 tau Proteins Proteins 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
-
- 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
- A61P25/24—Antidepressants
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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
- A61P25/28—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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0104340A SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | New compounds |
| PCT/SE2002/002373 WO2003053330A2 (en) | 2001-12-20 | 2002-12-18 | Use of oxindole derivatives in the treatment of dementia related diseases, alzheimer’s disease and conditions associated with glycogen synthase kinase-3 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009201189A Division JP2009280618A (ja) | 2001-12-20 | 2009-09-01 | 新規な化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005513082A JP2005513082A (ja) | 2005-05-12 |
| JP2005513082A5 JP2005513082A5 (https=) | 2009-10-22 |
| JP4465188B2 true JP4465188B2 (ja) | 2010-05-19 |
Family
ID=20286439
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554090A Expired - Fee Related JP4465188B2 (ja) | 2001-12-20 | 2002-12-18 | 新規な化合物 |
| JP2009201189A Pending JP2009280618A (ja) | 2001-12-20 | 2009-09-01 | 新規な化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009201189A Pending JP2009280618A (ja) | 2001-12-20 | 2009-09-01 | 新規な化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7205314B2 (https=) |
| EP (1) | EP1458707B1 (https=) |
| JP (2) | JP4465188B2 (https=) |
| AT (1) | ATE361287T1 (https=) |
| AU (1) | AU2002359164A1 (https=) |
| DE (1) | DE60219954T2 (https=) |
| ES (1) | ES2284964T3 (https=) |
| SE (1) | SE0104340D0 (https=) |
| WO (1) | WO2003053330A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1458711B1 (en) | 2001-12-21 | 2007-07-18 | AstraZeneca AB | Use of oxindole derivatives in the treatment of dementia related diseases, alzheimer s disease and conditions associated with glycogen synthase kinase-3 |
| SE0200979D0 (sv) * | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| SE0302546D0 (sv) * | 2003-09-24 | 2003-09-24 | Astrazeneca Ab | New compounds |
| CA2518465A1 (en) | 2003-03-25 | 2004-10-14 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| JP2007511467A (ja) | 2003-05-14 | 2007-05-10 | タケダ サン ディエゴ インコーポレイテッド | ジペプチジルペプチダーゼインヒビター |
| KR20060041309A (ko) | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | ４-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
| ES2319539T3 (es) | 2003-09-17 | 2009-05-08 | Janssen Pharmaceutica Nv | Compuestos heterociclicos condensados como moduladores del receptor de serotonina. |
| WO2006023931A2 (en) | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| CN101213187B (zh) | 2005-06-28 | 2012-06-06 | 塞诺菲-安万特股份有限公司 | 作为rho-激酶抑制剂的异喹啉衍生物 |
| CA2615577C (en) | 2005-07-26 | 2014-09-09 | Sanofi-Aventis | Piperidinyl-substituted isoquinolone derivatives as rho-kinase inhibitors |
| RS52241B (sr) | 2005-07-26 | 2012-10-31 | Sanofi | Derivati cikloheksilamin izohinolona kao inhibitori rho-kinaze |
| US7598255B2 (en) | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| MY147393A (en) | 2005-09-14 | 2012-11-30 | Takeda Pharmaceutical | Administration of dipeptidyl peptidase inhibitors |
| CA2622642C (en) | 2005-09-16 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| US20070287707A1 (en) * | 2006-02-28 | 2007-12-13 | Arrington Mark P | Phosphodiesterase 10 inhibitors |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| WO2007112347A1 (en) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7851468B2 (en) * | 2006-05-15 | 2010-12-14 | Cephalon, Inc. | Substituted pyrazolo[3,4-d]pyrimidines |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| SG158147A1 (en) | 2006-10-09 | 2010-01-29 | Takeda Pharmaceutical | Kinase inhibitors |
| CN101573352A (zh) | 2006-10-21 | 2009-11-04 | 艾博特股份有限两合公司 | 杂环化合物和其作为糖原合酶激酶3抑制剂的用途 |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| NZ577980A (en) | 2006-12-27 | 2012-01-12 | Sanofi Aventis | Cycloalkylamine substituted isoquinolone derivatives |
| JP5421783B2 (ja) | 2006-12-27 | 2014-02-19 | サノフイ | Ｒｈｏキナーゼ阻害剤としての置換イソキノロン及びイソキノリノン誘導体 |
| MX2009005964A (es) | 2006-12-27 | 2009-06-15 | Sanofi Aventis | Derivados de isoquinolina sustituidos con cicloalquilamina. |
| BRPI0720986A2 (pt) | 2006-12-27 | 2014-03-11 | Sanofi Aventis | Derivados de isoquinolina e isoquinolinona substituídos |
| MY148902A (en) | 2006-12-27 | 2013-06-14 | Sanofi Aventis | Substituted isoquinolines and their use as rho-kinase inhibitors |
| RU2468011C2 (ru) | 2006-12-27 | 2012-11-27 | Санофи-Авентис | Замещенные циклоалкиламином производные изохинолина и изохинолинона |
| PT2125744E (pt) | 2006-12-27 | 2011-07-01 | Sanofi Aventis | Derivados de isoquinolona e isoquinolinona substituídos com cicloalquilamina |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| US20090291982A1 (en) * | 2008-05-22 | 2009-11-26 | Astrazeneca Ab | New Substituted Oxindole Derivative 352 |
| MY153615A (en) | 2008-06-24 | 2015-02-27 | Sanofi Aventis | 6-substituted isoquinolines and isoquinolinones |
| MY153756A (en) | 2008-06-24 | 2015-03-13 | Sanofi Aventis | Bi-and polycyclic substituted isoquinoline and isoquinoline derivatives as rho kinase inhibitors |
| CA2728137C (en) | 2008-06-24 | 2016-10-18 | Sanofi-Aventis | Substituted isoquinolines and isoquinolinones as rho kinase inhibitors |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| TW201040191A (en) | 2009-03-27 | 2010-11-16 | Abbott Gmbh & Co Kg | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| MX336726B (es) * | 2010-09-27 | 2016-01-27 | Abbott Gmbh & Co Kg | Compuestos heterociclicos y su uso como inhibidores de la glucogeno sintasa quinasa-3. |
| US9090592B2 (en) | 2010-12-30 | 2015-07-28 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| US20240423998A1 (en) | 2021-11-29 | 2024-12-26 | Woolsey Pharmaceuticals, Inc. | Methods of treating agitation and other dementia-associated behavioral symptoms |
Family Cites Families (5)
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| TW530047B (en) | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
| ES2289791T3 (es) * | 1997-08-22 | 2008-02-01 | Astrazeneca Ab | Derivados de oxindolilquinazolina como inhibidores de la angiogenesis. |
| CA2340701C (en) * | 1998-08-20 | 2009-05-26 | Sumitomo Pharmaceuticals Co., Ltd. | Oxindole derivatives as growth hormone releasers |
| EP1136493A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-(Thienopyridinyl)pyrimidone, 2-(furopyridinyl)pyrimidone 2-(isoquinolinyl)pyrimidone, 2-(pyridoindolyl)pyrimidone and 2-(benzofuropyridinyl)pyrimidone derivatives |
-
2001
- 2001-12-20 SE SE0104340A patent/SE0104340D0/xx unknown
-
2002
- 2002-12-18 AT AT02793678T patent/ATE361287T1/de not_active IP Right Cessation
- 2002-12-18 AU AU2002359164A patent/AU2002359164A1/en not_active Abandoned
- 2002-12-18 ES ES02793678T patent/ES2284964T3/es not_active Expired - Lifetime
- 2002-12-18 JP JP2003554090A patent/JP4465188B2/ja not_active Expired - Fee Related
- 2002-12-18 DE DE60219954T patent/DE60219954T2/de not_active Expired - Lifetime
- 2002-12-18 EP EP02793678A patent/EP1458707B1/en not_active Expired - Lifetime
- 2002-12-18 WO PCT/SE2002/002373 patent/WO2003053330A2/en not_active Ceased
- 2002-12-18 US US10/499,217 patent/US7205314B2/en not_active Expired - Fee Related
-
2009
- 2009-09-01 JP JP2009201189A patent/JP2009280618A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009280618A (ja) | 2009-12-03 |
| EP1458707A2 (en) | 2004-09-22 |
| SE0104340D0 (sv) | 2001-12-20 |
| WO2003053330A3 (en) | 2003-10-30 |
| DE60219954D1 (de) | 2007-06-14 |
| DE60219954T2 (de) | 2008-01-17 |
| US20050065170A1 (en) | 2005-03-24 |
| JP2005513082A (ja) | 2005-05-12 |
| US7205314B2 (en) | 2007-04-17 |
| AU2002359164A8 (en) | 2003-07-09 |
| AU2002359164A1 (en) | 2003-07-09 |
| WO2003053330A2 (en) | 2003-07-03 |
| EP1458707B1 (en) | 2007-05-02 |
| ATE361287T1 (de) | 2007-05-15 |
| ES2284964T3 (es) | 2007-11-16 |
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