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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 108091026813 Poly(ADPribose) Proteins 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
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 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
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 208000028867 ischemia Diseases 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
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005842 heteroatom 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
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
- -1 C 1 -C 6 alkyl Chemical class 0.000 claims description 5
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims description 5
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims description 5
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 201000011510 cancer Diseases 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 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
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 230000010410 reperfusion Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 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
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-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
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 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 atom Chemical class [H]* 0.000 claims 6
- 230000006378 damage Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 208000001408 Carbon monoxide poisoning Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 208000016192 Demyelinating disease Diseases 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000003792 cranial nerve Anatomy 0.000 description 1
- 208000029039 cyanide poisoning Diseases 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 208000003906 hydrocephalus Diseases 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000019420 lymphoid neoplasm Diseases 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 208000032253 retinal ischemia Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 210000005166 vasculature Anatomy 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 (enExample) | 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)
| Country | Link |
|---|---|
| US (3) | US8299090B2 (enExample) |
| EP (2) | EP2303895B1 (enExample) |
| JP (2) | JP5564495B2 (enExample) |
| AR (1) | AR072265A1 (enExample) |
| AU (1) | AU2009260060B2 (enExample) |
| CA (1) | CA2728454C (enExample) |
| DK (1) | DK2303895T3 (enExample) |
| ES (1) | ES2530815T3 (enExample) |
| HK (1) | HK1212698A1 (enExample) |
| SA (1) | SA109300394B1 (enExample) |
| TW (1) | TWI471329B (enExample) |
| WO (1) | WO2009155402A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SA109300394B1 (ar) * | 2008-06-19 | 2013-01-22 | ويث | ثيازوليل- وأوكسازوليل- أيزوكوينولينونات وطرق لاستخدامها |
| JP5632368B2 (ja) | 2008-06-19 | 2014-11-26 | ワイス・エルエルシー | チエニル−およびフラニル−イソキノリノン、ならびにそれらの使用方法 |
| CN103957711A (zh) | 2011-07-04 | 2014-07-30 | 拜耳知识产权有限责任公司 | 取代的异喹啉酮、异喹啉二酮、异喹啉三酮和二氢异喹啉酮或其各自的盐作为活性剂对抗植物非生物胁迫的用途 |
| 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 |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | 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 |
| WO2024261243A1 (en) | 2023-06-21 | 2024-12-26 | Hemispherian As | Combination comprising a deoxycytidine derivative and a parp inhibitor for use in a method of treating hr proficient cancer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2963332D1 (en) * | 1978-05-26 | 1982-09-02 | Lepetit Spa | 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 |
| ATE540928T1 (de) * | 2002-11-22 | 2012-01-15 | Mitsubishi Tanabe Pharma Corp | Isochinolinverbindungen und ihre medizinische verwendung |
| ATE533812T1 (de) | 2005-08-01 | 2011-12-15 | Wietek Holding Gmbh | Verfahren zur rezyklierung von kunststoff |
| ES2559679T3 (es) | 2006-06-20 | 2016-02-15 | Abbvie Inc. | Pirazoloquinazolinonas como inhibidores de PARP |
| SA109300394B1 (ar) * | 2008-06-19 | 2013-01-22 | ويث | ثيازوليل- وأوكسازوليل- أيزوكوينولينونات وطرق لاستخدامها |
| JP5632368B2 (ja) * | 2008-06-19 | 2014-11-26 | ワイス・エルエルシー | チエニル−およびフラニル−イソキノリノン、ならびにそれらの使用方法 |
-
2009
- 2009-06-17 SA SA109300394A patent/SA109300394B1/ar unknown
- 2009-06-18 ES ES09767711T patent/ES2530815T3/es active Active
- 2009-06-18 EP EP09767711.6A patent/EP2303895B1/en active Active
- 2009-06-18 JP JP2011514801A patent/JP5564495B2/ja not_active Expired - Fee Related
- 2009-06-18 DK DK09767711.6T patent/DK2303895T3/en active
- 2009-06-18 WO PCT/US2009/047767 patent/WO2009155402A1/en not_active Ceased
- 2009-06-18 EP EP14185672.4A patent/EP2896626A1/en not_active Withdrawn
- 2009-06-18 CA CA2728454A patent/CA2728454C/en active Active
- 2009-06-18 AU AU2009260060A patent/AU2009260060B2/en not_active Ceased
- 2009-06-18 US US12/487,247 patent/US8299090B2/en not_active Expired - Fee Related
- 2009-06-19 AR ARP090102266A patent/AR072265A1/es active IP Right Grant
- 2009-06-19 TW TW98120713A patent/TWI471329B/zh not_active IP Right Cessation
-
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/en unknown