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 |
| CA2728466A1 (en) * | 2008-06-19 | 2009-12-23 | Wyeth Llc | Thienyl- and furanyl-isoquinolinones and methods for using them |
| 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 |
| ES2562903T3 (es) * | 2011-07-13 | 2016-03-09 | Santen Pharmaceutical Co., Ltd | Nuevo compuesto que tiene actividad inhibidora de PARP |
| ES2879434T3 (es) | 2015-07-23 | 2021-11-22 | Inst Curie | Uso de una combinación de molécula Dbait e inhibidores de PARP para tratamiento del cáncer |
| 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 |
| US20200407720A1 (en) | 2018-03-13 | 2020-12-31 | 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 |
| CN121398822A (zh) | 2023-06-21 | 2026-01-23 | 四方生物科学有限公司 | 用于在治疗hr功能正常的癌症的方法中的用途的包含脱氧胞苷衍生物和parp抑制剂的组合 |
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 |
| AU2003284632A1 (en) * | 2002-11-22 | 2004-06-18 | Mitsubishi Pharma Corporation | Isoquinoline compounds and medicinal use thereof |
| WO2007014907A1 (en) | 2005-08-01 | 2007-02-08 | Wietek Holding Gmbh | Process for the recycling of plastics |
| 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 |
| CA2728466A1 (en) * | 2008-06-19 | 2009-12-23 | Wyeth Llc | Thienyl- and furanyl-isoquinolinones and methods for using them |
-
2009
- 2009-06-17 SA SA109300394A patent/SA109300394B1/ar unknown
- 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 AU AU2009260060A patent/AU2009260060B2/en not_active Ceased
- 2009-06-18 DK DK09767711.6T patent/DK2303895T3/en active
- 2009-06-18 CA CA2728454A patent/CA2728454C/en active Active
- 2009-06-18 EP EP14185672.4A patent/EP2896626A1/en not_active Withdrawn
- 2009-06-18 ES ES09767711T patent/ES2530815T3/es active Active
- 2009-06-18 WO PCT/US2009/047767 patent/WO2009155402A1/en not_active Ceased
- 2009-06-18 US US12/487,247 patent/US8299090B2/en not_active Expired - Fee Related
- 2009-06-19 TW TW98120713A patent/TWI471329B/zh not_active IP Right Cessation
- 2009-06-19 AR ARP090102266A patent/AR072265A1/es active IP Right Grant
-
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
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