ES2259419T3 - Imidazo(1,2-a)piridinas. - Google Patents
Imidazo(1,2-a)piridinas.Info
- Publication number
- ES2259419T3 ES2259419T3 ES03766355T ES03766355T ES2259419T3 ES 2259419 T3 ES2259419 T3 ES 2259419T3 ES 03766355 T ES03766355 T ES 03766355T ES 03766355 T ES03766355 T ES 03766355T ES 2259419 T3 ES2259419 T3 ES 2259419T3
- Authority
- ES
- Spain
- Prior art keywords
- pyridin
- alkyl
- methyl
- mmol
- hydrogen
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 125000005843 halogen group Chemical group 0.000 claims abstract description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 239000000460 chlorine Substances 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- -1 -CF 3 Chemical group 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- NPPIXSXSFGFFON-UHFFFAOYSA-N 3-[2-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-4-yl]-2-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 NPPIXSXSFGFFON-UHFFFAOYSA-N 0.000 claims description 11
- CQTUYMRZAZVKDQ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(4-methylsulfonylphenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 CQTUYMRZAZVKDQ-UHFFFAOYSA-N 0.000 claims description 10
- XGGCDVFQPLAMKA-UHFFFAOYSA-N 7-methyl-2-(6-methylpyridin-2-yl)-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound N1=C2C=C(C)C=CN2C(C=2C=C(N=CC=2)C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC(C)=N1 XGGCDVFQPLAMKA-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 208000017169 kidney disease Diseases 0.000 claims description 10
- CCGRXCIJCYWWOY-UHFFFAOYSA-N 4-[4-[4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 CCGRXCIJCYWWOY-UHFFFAOYSA-N 0.000 claims description 9
- NQQMVZUQPDMLHG-UHFFFAOYSA-N 4-[[4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]methyl]morpholine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)=N1 NQQMVZUQPDMLHG-UHFFFAOYSA-N 0.000 claims description 9
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- YSMRWZHDCKWGEE-UHFFFAOYSA-N [4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=N1 YSMRWZHDCKWGEE-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
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- SFHCTSWZYNNONF-UHFFFAOYSA-N 2-pyridin-2-yl-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C=1C=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=CC=1OCCN1CCCC1 SFHCTSWZYNNONF-UHFFFAOYSA-N 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
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- 230000005855 radiation Effects 0.000 description 1
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- 238000006268 reductive amination reaction Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003355 serines Chemical group 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
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- 230000015590 smooth muscle cell migration Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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- 231100000216 vascular lesion Toxicity 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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Classifications
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0217783 | 2002-07-31 | ||
| GBGB0217783.0A GB0217783D0 (en) | 2002-07-31 | 2002-07-31 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2259419T3 true ES2259419T3 (es) | 2006-10-01 |
Family
ID=9941484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03766355T Expired - Lifetime ES2259419T3 (es) | 2002-07-31 | 2003-07-29 | Imidazo(1,2-a)piridinas. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20050234029A1 (OSRAM) |
| EP (1) | EP1543003B1 (OSRAM) |
| JP (1) | JP2005537291A (OSRAM) |
| AR (1) | AR040724A1 (OSRAM) |
| AT (1) | ATE326467T1 (OSRAM) |
| AU (1) | AU2003255323A1 (OSRAM) |
| DE (1) | DE60305332T2 (OSRAM) |
| ES (1) | ES2259419T3 (OSRAM) |
| GB (1) | GB0217783D0 (OSRAM) |
| TW (1) | TW200413366A (OSRAM) |
| WO (1) | WO2004013138A2 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| AU2003260345A1 (en) * | 2002-07-31 | 2004-02-23 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
| UA80296C2 (en) * | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| KR20080000665A (ko) | 2005-04-22 | 2008-01-02 | 알란토스 파마슈티컬즈 홀딩, 인코포레이티드 | 디펩티딜 펩티다아제-ⅳ 억제제 |
| JP2009507032A (ja) * | 2005-09-02 | 2009-02-19 | アボット・ラボラトリーズ | 新規なイミダゾ系複素環 |
| CN101611007A (zh) | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| US20100298314A1 (en) * | 2006-12-20 | 2010-11-25 | Schering Corporation | Novel jnk inhibitors |
| BRPI0817434A2 (pt) | 2007-10-17 | 2015-06-16 | Novartis Ag | Composto orgânicos |
| BRPI0822237A2 (pt) * | 2007-12-21 | 2015-06-30 | Wyeth Llc | Compostos de imidazo [1,2-a] piridina |
| JP5507543B2 (ja) * | 2008-04-29 | 2014-05-28 | ノバルティス アーゲー | アクチビン様受容体キナーゼ（ａｌｋ４またはａｌｋ５）阻害剤としてのイミダゾ−ピリジン誘導体 |
| NZ599597A (en) | 2009-10-30 | 2013-05-31 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| MX2012006994A (es) * | 2009-12-18 | 2012-07-03 | Mitsubishi Tanabe Pharma Corp | Agente antiplaquetas novedoso. |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| WO2011146287A1 (en) | 2010-05-20 | 2011-11-24 | Takeda Pharmaceutical Company Limited | Pyrazolo[4,3-b]pyridine-7-amine inhibitors of alk5 |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| ES2575092T3 (es) | 2011-06-27 | 2016-06-24 | Janssen Pharmaceutica, N.V. | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina |
| RU2657540C2 (ru) | 2012-06-26 | 2018-06-14 | Янссен Фармацевтика Нв | Комбинации, содержащие ингибиторы pde 2, такие как 1-арил-4-метил-[1,2,4]триазоло[4,3-а]хиноксалиновые соединения, и ингибиторы pde 10, для применения в лечении неврологических или метаболических расстройств |
| KR102171706B1 (ko) | 2012-07-09 | 2020-10-30 | 얀센 파마슈티카 엔.브이. | 포스포디에스테라아제 10 효소의 억제제 |
| CN108341769A (zh) * | 2018-05-13 | 2018-07-31 | 浙江凯普化工有限公司 | 多取代的6-氟皮考啉酸的制备方法 |
| CN115975224B (zh) * | 2023-03-16 | 2023-08-08 | 四川大学 | 一种pH/ROS双响应的组织粘附载药水凝胶及其制备方法和应用 |
Family Cites Families (7)
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|---|---|---|---|---|
| JPH11302177A (ja) * | 1998-04-27 | 1999-11-02 | Otsuka Pharmaceut Factory Inc | 腎炎治療剤 |
| GB0007405D0 (en) * | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| JP2004517068A (ja) * | 2000-11-16 | 2004-06-10 | スミスクライン・ビーチャム・コーポレイション | 化合物 |
| GB0027987D0 (en) * | 2000-11-16 | 2001-01-03 | Smithkline Beecham Plc | Compounds |
| GB0100762D0 (en) * | 2001-01-11 | 2001-02-21 | Smithkline Beecham Plc | Novel use |
| AU2003260345A1 (en) * | 2002-07-31 | 2004-02-23 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
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2002
- 2002-07-31 GB GBGB0217783.0A patent/GB0217783D0/en not_active Ceased
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2003
- 2003-07-29 US US10/522,967 patent/US20050234029A1/en not_active Abandoned
- 2003-07-29 AR AR20030102720A patent/AR040724A1/es not_active Application Discontinuation
- 2003-07-29 WO PCT/EP2003/008390 patent/WO2004013138A2/en not_active Ceased
- 2003-07-29 DE DE60305332T patent/DE60305332T2/de not_active Expired - Fee Related
- 2003-07-29 EP EP03766355A patent/EP1543003B1/en not_active Expired - Lifetime
- 2003-07-29 TW TW092120589A patent/TW200413366A/zh unknown
- 2003-07-29 ES ES03766355T patent/ES2259419T3/es not_active Expired - Lifetime
- 2003-07-29 JP JP2004525375A patent/JP2005537291A/ja active Pending
- 2003-07-29 AU AU2003255323A patent/AU2003255323A1/en not_active Abandoned
- 2003-07-29 AT AT03766355T patent/ATE326467T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1543003A2 (en) | 2005-06-22 |
| US20050234029A1 (en) | 2005-10-20 |
| AR040724A1 (es) | 2005-04-20 |
| AU2003255323A8 (en) | 2004-02-23 |
| JP2005537291A (ja) | 2005-12-08 |
| ATE326467T1 (de) | 2006-06-15 |
| WO2004013138A3 (en) | 2004-03-25 |
| EP1543003B1 (en) | 2006-05-17 |
| WO2004013138A2 (en) | 2004-02-12 |
| AU2003255323A1 (en) | 2004-02-23 |
| DE60305332D1 (de) | 2006-06-22 |
| DE60305332T2 (de) | 2007-04-19 |
| TW200413366A (en) | 2004-08-01 |
| GB0217783D0 (en) | 2002-09-11 |
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