JP2011525185A5 - - Google Patents
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- Publication number
- JP2011525185A5 JP2011525185A5 JP2011514801A JP2011514801A JP2011525185A5 JP 2011525185 A5 JP2011525185 A5 JP 2011525185A5 JP 2011514801 A JP2011514801 A JP 2011514801A JP 2011514801 A JP2011514801 A JP 2011514801A JP 2011525185 A5 JP2011525185 A5 JP 2011525185A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- isoquinolin
- hydroxy
- thiazolo
- composition
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229920001422 Poly(ADPribose) Polymers 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003839 salts Chemical group 0.000 claims description 12
- 206010053643 Neurodegenerative disease Diseases 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 206010061255 Ischaemia Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- -1 alkynylene compound Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- 125000005842 heteroatoms Chemical group 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims description 5
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 125000004429 atoms Chemical group 0.000 claims description 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
- 230000016273 neuron death Effects 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- HDRITKBVBOESHB-UHFFFAOYSA-N 2-(3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-ylmethyl)-9-hydroxy-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1CCC2CCCCC2N1CC1=NC(C2=C(C(N3)=O)C=CC=C2O)=C3S1 HDRITKBVBOESHB-UHFFFAOYSA-N 0.000 claims description 2
- OKIORNRGRJGNDT-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-9-hydroxy-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1=CC(O)=C2C(N=C(S3)CN(C)C)=C3NC(=O)C2=C1 OKIORNRGRJGNDT-UHFFFAOYSA-N 0.000 claims description 2
- UFGKEUKYVUYZPF-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1=CC=C2C(N=C(S3)CCN(C)C)=C3NC(=O)C2=C1 UFGKEUKYVUYZPF-UHFFFAOYSA-N 0.000 claims description 2
- QFYOLODDTBRVSH-UHFFFAOYSA-N 2-[3-(dimethylamino)prop-1-ynyl]-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1=CC=C2C(N=C(S3)C#CCN(C)C)=C3NC(=O)C2=C1 QFYOLODDTBRVSH-UHFFFAOYSA-N 0.000 claims description 2
- VTYYKKIMVNWVEB-PHIMTYICSA-N 2-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]methyl]-9-hydroxy-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C[C@H]1CCC[C@@H](C)N1CC(S1)=NC2=C1NC(=O)C1=CC=CC(O)=C21 VTYYKKIMVNWVEB-PHIMTYICSA-N 0.000 claims description 2
- HGVOVHQTFMXKDZ-AOOOYVTPSA-N 2-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-9-hydroxy-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC(S1)=NC2=C1NC(=O)C1=CC=CC(O)=C21 HGVOVHQTFMXKDZ-AOOOYVTPSA-N 0.000 claims description 2
- VKHNODUXUOMNKR-SNVBAGLBSA-N 2-[[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-9-hydroxy-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound C1[C@H](N(C)C)CCN1CC(S1)=NC2=C1NC(=O)C1=CC=CC(O)=C21 VKHNODUXUOMNKR-SNVBAGLBSA-N 0.000 claims description 2
- HIALQSRLCAFPJR-UHFFFAOYSA-N 9-hydroxy-2-(morpholin-4-ylmethyl)-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound OC1=CC=CC(C(NC=2S3)=O)=C1C=2N=C3CN1CCOCC1 HIALQSRLCAFPJR-UHFFFAOYSA-N 0.000 claims description 2
- KXXIEYFYYLEDAM-UHFFFAOYSA-N 9-hydroxy-2-(piperidin-1-ylmethyl)-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound OC1=CC=CC(C(NC=2S3)=O)=C1C=2N=C3CN1CCCCC1 KXXIEYFYYLEDAM-UHFFFAOYSA-N 0.000 claims description 2
- VCOZPOCXDYPYDE-UHFFFAOYSA-N 9-hydroxy-2-(pyrrolidin-1-ylmethyl)-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound OC1=CC=CC(C(NC=2S3)=O)=C1C=2N=C3CN1CCCC1 VCOZPOCXDYPYDE-UHFFFAOYSA-N 0.000 claims description 2
- HNNWMLHDFNJBTE-UHFFFAOYSA-N 9-hydroxy-2-[(2-methylpyrrolidin-1-yl)methyl]-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound CC1CCCN1CC(S1)=NC2=C1NC(=O)C1=CC=CC(O)=C21 HNNWMLHDFNJBTE-UHFFFAOYSA-N 0.000 claims description 2
- KBEYEYKPUJXEOF-SNVBAGLBSA-N 9-hydroxy-2-[[(2R)-2-(trifluoromethyl)pyrrolidin-1-yl]methyl]-4H-[1,3]thiazolo[5,4-c]isoquinolin-5-one Chemical compound OC1=CC=CC(C(NC=2S3)=O)=C1C=2N=C3CN1CCC[C@@H]1C(F)(F)F KBEYEYKPUJXEOF-SNVBAGLBSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N Azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- VMWJCFLUSKZZDX-UHFFFAOYSA-N N,N-dimethylmethanamine Chemical group [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004946 alkenylalkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 229940113083 morpholine Drugs 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 13
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 3
- 201000010099 disease Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- 206010000565 Acquired immunodeficiency syndrome Diseases 0.000 description 1
- 206010001897 Alzheimer's disease Diseases 0.000 description 1
- 206010002026 Amyotrophic lateral sclerosis Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 210000000988 Bone and Bones Anatomy 0.000 description 1
- 208000001183 Brain Injury Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 206010007515 Cardiac arrest Diseases 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010009887 Colitis Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 210000003792 Cranial Nerves Anatomy 0.000 description 1
- 206010011401 Crohn's disease Diseases 0.000 description 1
- 208000004275 Demyelinating Disease Diseases 0.000 description 1
- 206010012601 Diabetes mellitus Diseases 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 206010015037 Epilepsy Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 201000001971 Huntington's disease Diseases 0.000 description 1
- 208000003906 Hydrocephalus Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 210000000987 Immune System Anatomy 0.000 description 1
- 206010022114 Injury Diseases 0.000 description 1
- 206010024324 Leukaemias Diseases 0.000 description 1
- 208000002780 Macular Degeneration Diseases 0.000 description 1
- 210000003205 Muscles Anatomy 0.000 description 1
- 208000003627 Muscular Dystrophy Diseases 0.000 description 1
- 208000004296 Neuralgia Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010061536 Parkinson's disease Diseases 0.000 description 1
- 208000001293 Peripheral Nervous System Disease Diseases 0.000 description 1
- 206010034606 Peripheral neuropathy Diseases 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 201000001320 atherosclerosis Diseases 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000002490 cerebral Effects 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 200000000018 inflammatory disease Diseases 0.000 description 1
- 230000000968 intestinal Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000000607 poisoning Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 201000001365 retinal ischemia Diseases 0.000 description 1
- 201000010874 syndrome Diseases 0.000 description 1
- 201000006704 ulcerative colitis Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7385708P | 2008-06-19 | 2008-06-19 | |
| US61/073,857 | 2008-06-19 | ||
| PCT/US2009/047767 WO2009155402A1 (en) | 2008-06-19 | 2009-06-18 | Thiazolyl- and oxazolyl-isoquinolinones and methods for using them |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014067493A Division JP2014122242A (ja) | 2008-06-19 | 2014-03-28 | チアゾリル−およびオキサゾリル−イソキノリノン、ならびにそれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011525185A JP2011525185A (ja) | 2011-09-15 |
| JP2011525185A5 true JP2011525185A5 (US07794700-20100914-C00152.png) | 2012-08-02 |
| JP5564495B2 JP5564495B2 (ja) | 2014-07-30 |
Family
ID=41087350
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011514801A Expired - Fee Related JP5564495B2 (ja) | 2008-06-19 | 2009-06-18 | チアゾリル−およびオキサゾリル−イソキノリノン、ならびにそれらの使用方法 |
| JP2014067493A Withdrawn JP2014122242A (ja) | 2008-06-19 | 2014-03-28 | チアゾリル−およびオキサゾリル−イソキノリノン、ならびにそれらの使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014067493A Withdrawn JP2014122242A (ja) | 2008-06-19 | 2014-03-28 | チアゾリル−およびオキサゾリル−イソキノリノン、ならびにそれらの使用方法 |
Country Status (12)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009155413A1 (en) * | 2008-06-19 | 2009-12-23 | Wyeth | Thienyl- and furanyl-isoquinolinones and methods for using them |
| SA109300394B1 (ar) | 2008-06-19 | 2013-01-22 | ويث | ثيازوليل- وأوكسازوليل- أيزوكوينولينونات وطرق لاستخدامها |
| EP2729007A1 (de) | 2011-07-04 | 2014-05-14 | Bayer Intellectual Property GmbH | Verwendung substituierter isochinolinone, isochinolindione, isochinolintrione und dihydroisochinolinone oder jeweils deren salze als wirkstoffe gegen abiotischen pflanzenstress |
| CA2841897A1 (en) * | 2011-07-13 | 2013-01-17 | Santen Pharmaceutical Co., Ltd. | Novel compound having parp inhibitory activity |
| EP3325623B3 (en) | 2015-07-23 | 2021-01-20 | Institut Curie | Use of a combination of dbait molecule and parp inhibitors to treat cancer |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
| WO2019175132A1 (en) | 2018-03-13 | 2019-09-19 | Onxeo | A dbait molecule against acquired resistance in the treatment of cancer |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005745B1 (en) * | 1978-05-26 | 1982-07-14 | Gruppo Lepetit S.P.A. | Pyrazolo (3,4-c) and thiazolo (5,4-c) isoquinolines, methods for preparing them, these compounds for use as antiinflammatory, cns-depressant and anti-anxiety agents and pharmaceutical compositions thereof |
| ITMI20002358A1 (it) * | 2000-10-31 | 2002-05-01 | Flavio Moroni | Derivati di tieno ,2, 3-c|isochinolin-3-one come inibitori della poli(a dp-ribosio)polimerasi |
| AUPS137402A0 (en) * | 2002-03-26 | 2002-05-09 | Fujisawa Pharmaceutical Co., Ltd. | Novel tricyclic compounds |
| EP1566380B1 (en) * | 2002-11-22 | 2012-01-11 | Mitsubishi Tanabe Pharma Corporation | Isoquinoline compounds and medicinal use thereof |
| US7696255B2 (en) | 2005-08-01 | 2010-04-13 | Wietek Holding Gmbh | Process for the recycling of plastics |
| CN101506214A (zh) * | 2006-06-20 | 2009-08-12 | 艾博特公司 | 作为parp抑制剂的吡唑并喹唑啉酮 |
| WO2009155413A1 (en) * | 2008-06-19 | 2009-12-23 | Wyeth | Thienyl- and furanyl-isoquinolinones and methods for using them |
| SA109300394B1 (ar) * | 2008-06-19 | 2013-01-22 | ويث | ثيازوليل- وأوكسازوليل- أيزوكوينولينونات وطرق لاستخدامها |
-
2009
- 2009-06-17 SA SA109300394A patent/SA109300394B1/ar unknown
- 2009-06-18 EP EP14185672.4A patent/EP2896626A1/en not_active Withdrawn
- 2009-06-18 EP EP09767711.6A patent/EP2303895B1/en active Active
- 2009-06-18 ES ES09767711T patent/ES2530815T3/es active Active
- 2009-06-18 DK DK09767711.6T patent/DK2303895T3/en active
- 2009-06-18 WO PCT/US2009/047767 patent/WO2009155402A1/en active Application Filing
- 2009-06-18 JP JP2011514801A patent/JP5564495B2/ja not_active Expired - Fee Related
- 2009-06-18 CA CA2728454A patent/CA2728454C/en active Active
- 2009-06-18 US US12/487,247 patent/US8299090B2/en active Active
- 2009-06-18 AU AU2009260060A patent/AU2009260060B2/en active Active
- 2009-06-19 TW TW98120713A patent/TWI471329B/zh active
- 2009-06-19 AR ARP090102266A patent/AR072265A1/es active IP Right Grant
-
2011
- 2011-10-06 HK HK11110561.5A patent/HK1156310A1/xx unknown
-
2012
- 2012-10-18 US US13/655,082 patent/US8906935B2/en active Active
-
2014
- 2014-03-28 JP JP2014067493A patent/JP2014122242A/ja not_active Withdrawn
- 2014-11-07 US US14/535,877 patent/US9265769B2/en active Active
-
2016
- 2016-01-21 HK HK16100665.6A patent/HK1212698A1/zh unknown
