EA016177B1 - Соединения имидазолидинониламинопиримидина для лечения рака - Google Patents
Соединения имидазолидинониламинопиримидина для лечения рака Download PDFInfo
- Publication number
- EA016177B1 EA016177B1 EA200970615A EA200970615A EA016177B1 EA 016177 B1 EA016177 B1 EA 016177B1 EA 200970615 A EA200970615 A EA 200970615A EA 200970615 A EA200970615 A EA 200970615A EA 016177 B1 EA016177 B1 EA 016177B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- thiophen
- benzo
- ethyl
- imidazolidin
- ylamino
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title abstract description 13
- 201000011510 cancer Diseases 0.000 title abstract description 11
- VLUNZXPZDFIDHY-UHFFFAOYSA-N 1-(2-aminopyrimidin-4-yl)imidazolidin-2-one Chemical class NC1=NC=CC(N2C(NCC2)=O)=N1 VLUNZXPZDFIDHY-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- -1 C-Calkoxy Chemical group 0.000 claims abstract description 36
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 109
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
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- JSRKJTDNAHLIOE-UHFFFAOYSA-N 1-[2-[[4-[7-(3-aminopyridin-4-yl)-1-benzothiophen-2-yl]-5-fluoropyrimidin-2-yl]amino]ethyl]imidazolidin-2-one Chemical compound NC1=CN=CC=C1C1=CC=CC2=C1SC(C=1C(=CN=C(NCCN3C(NCC3)=O)N=1)F)=C2 JSRKJTDNAHLIOE-UHFFFAOYSA-N 0.000 claims description 3
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- IGOYEBNSIXBBAD-UHFFFAOYSA-N 1-[2-[[4-[7-(2-chloropyridin-4-yl)-1-benzothiophen-2-yl]-5-fluoropyrimidin-2-yl]amino]ethyl]imidazolidin-2-one Chemical compound N1=C(C=2SC3=C(C=4C=C(Cl)N=CC=4)C=CC=C3C=2)C(F)=CN=C1NCCN1CCNC1=O IGOYEBNSIXBBAD-UHFFFAOYSA-N 0.000 claims 1
- KUAGVMSXOALRBK-UHFFFAOYSA-N 1-[2-[[4-[7-(3-aminopyridin-4-yl)-1-benzothiophen-2-yl]pyrimidin-2-yl]amino]ethyl]imidazolidin-2-one Chemical compound NC1=CN=CC=C1C1=CC=CC2=C1SC(C=1N=C(NCCN3C(NCC3)=O)N=CC=1)=C2 KUAGVMSXOALRBK-UHFFFAOYSA-N 0.000 claims 1
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- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
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- 229940122803 Vinca alkaloid Drugs 0.000 description 1
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- 239000006286 aqueous extract Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 229950006137 dexfosfoserine Drugs 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IONSZLINWCGRRI-UHFFFAOYSA-N n'-hydroxymethanimidamide Chemical compound NC=NO IONSZLINWCGRRI-UHFFFAOYSA-N 0.000 description 1
- DBGFNLVRAFYZBI-UHFFFAOYSA-N n-methylpyridin-3-amine Chemical compound CNC1=CC=CN=C1 DBGFNLVRAFYZBI-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 201000010198 papillary carcinoma Diseases 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000012607 strong cation exchange resin Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- QPAZSNGSVRYMDE-UHFFFAOYSA-N tert-butyl n-(2-fluoropyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN=C1F QPAZSNGSVRYMDE-UHFFFAOYSA-N 0.000 description 1
- FXGNEIOGSGKPFL-UHFFFAOYSA-N tert-butyl n-(6-fluoropyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(F)N=C1 FXGNEIOGSGKPFL-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87130206P | 2006-12-21 | 2006-12-21 | |
| PCT/US2007/087044 WO2008076704A1 (en) | 2006-12-21 | 2007-12-11 | Imidazolidinonyl aminopyrimidine compounds for the treatment' of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200970615A1 EA200970615A1 (ru) | 2009-10-30 |
| EA016177B1 true EA016177B1 (ru) | 2012-02-28 |
Family
ID=39186811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200970615A EA016177B1 (ru) | 2006-12-21 | 2007-12-11 | Соединения имидазолидинониламинопиримидина для лечения рака |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8101628B2 (enExample) |
| EP (1) | EP2125793B1 (enExample) |
| JP (1) | JP5166441B2 (enExample) |
| KR (1) | KR101088291B1 (enExample) |
| CN (1) | CN101563342B (enExample) |
| AT (1) | ATE479680T1 (enExample) |
| AU (1) | AU2007334039B2 (enExample) |
| BR (1) | BRPI0721045A2 (enExample) |
| CA (1) | CA2671738A1 (enExample) |
| DE (1) | DE602007008952D1 (enExample) |
| EA (1) | EA016177B1 (enExample) |
| ES (1) | ES2349169T3 (enExample) |
| MX (1) | MX2009006634A (enExample) |
| WO (1) | WO2008076704A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA016178B1 (ru) | 2006-12-21 | 2012-02-28 | Эли Лилли Энд Компани | Соединения имидазолидинониламинопиримидина |
| EP2155735A2 (en) | 2007-05-16 | 2010-02-24 | Eli Lilly And Company | Triazolyl aminopyrimidine compounds |
| TW200908981A (en) * | 2007-05-16 | 2009-03-01 | Lilly Co Eli | Triazolyl aminopyrimidine compounds |
| CN108853111B (zh) * | 2018-08-07 | 2020-06-05 | 浙江大学 | 一种组合物在制备治疗吉非替尼肝脏毒性药物中的应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004063192A1 (en) * | 2003-01-10 | 2004-07-29 | Pharmacopeia Drug Discovery, Inc. | Imidazolyl pyrimidine derivatives useful as il-8 receptor modulators |
| WO2006066172A1 (en) * | 2004-12-17 | 2006-06-22 | Amgen, Inc. | Aminopyrimidine compounds and methods of use |
| WO2007092095A2 (en) * | 2005-11-18 | 2007-08-16 | Eli Lilly And Company | [4-(benzo [b] thi0phen-2-yl) pyrimidin-2yl] -amine derivatives as ikk-beta inhibitors for the treatment of cancer and inflammatory diseases. |
| WO2007117465A2 (en) * | 2006-03-31 | 2007-10-18 | Abbott Laboratories | Indazole compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4929726A (en) | 1988-02-09 | 1990-05-29 | Georgia State University Foundation, Inc. | Novel diazines and their method of preparation |
| US6939877B2 (en) * | 2002-09-12 | 2005-09-06 | Wyeth | Antidepressant piperidine derivatives of heterocycle-fused benzodioxans |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| WO2005012283A1 (en) * | 2003-07-31 | 2005-02-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted benzothiophene compounds and uses thereof |
| EA016178B1 (ru) | 2006-12-21 | 2012-02-28 | Эли Лилли Энд Компани | Соединения имидазолидинониламинопиримидина |
| EP2155735A2 (en) | 2007-05-16 | 2010-02-24 | Eli Lilly And Company | Triazolyl aminopyrimidine compounds |
| TW200908981A (en) | 2007-05-16 | 2009-03-01 | Lilly Co Eli | Triazolyl aminopyrimidine compounds |
-
2007
- 2007-12-11 AT AT07855058T patent/ATE479680T1/de not_active IP Right Cessation
- 2007-12-11 BR BRPI0721045-0A patent/BRPI0721045A2/pt not_active IP Right Cessation
- 2007-12-11 CN CN2007800472640A patent/CN101563342B/zh not_active Expired - Fee Related
- 2007-12-11 EP EP07855058A patent/EP2125793B1/en not_active Not-in-force
- 2007-12-11 US US12/516,514 patent/US8101628B2/en not_active Expired - Fee Related
- 2007-12-11 JP JP2009543061A patent/JP5166441B2/ja not_active Expired - Fee Related
- 2007-12-11 WO PCT/US2007/087044 patent/WO2008076704A1/en not_active Ceased
- 2007-12-11 CA CA002671738A patent/CA2671738A1/en not_active Abandoned
- 2007-12-11 MX MX2009006634A patent/MX2009006634A/es active IP Right Grant
- 2007-12-11 KR KR1020097012835A patent/KR101088291B1/ko not_active Expired - Fee Related
- 2007-12-11 ES ES07855058T patent/ES2349169T3/es active Active
- 2007-12-11 DE DE602007008952T patent/DE602007008952D1/de active Active
- 2007-12-11 AU AU2007334039A patent/AU2007334039B2/en not_active Ceased
- 2007-12-11 EA EA200970615A patent/EA016177B1/ru not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004063192A1 (en) * | 2003-01-10 | 2004-07-29 | Pharmacopeia Drug Discovery, Inc. | Imidazolyl pyrimidine derivatives useful as il-8 receptor modulators |
| WO2006066172A1 (en) * | 2004-12-17 | 2006-06-22 | Amgen, Inc. | Aminopyrimidine compounds and methods of use |
| WO2007092095A2 (en) * | 2005-11-18 | 2007-08-16 | Eli Lilly And Company | [4-(benzo [b] thi0phen-2-yl) pyrimidin-2yl] -amine derivatives as ikk-beta inhibitors for the treatment of cancer and inflammatory diseases. |
| WO2007117465A2 (en) * | 2006-03-31 | 2007-10-18 | Abbott Laboratories | Indazole compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101563342A (zh) | 2009-10-21 |
| CN101563342B (zh) | 2012-09-05 |
| US8101628B2 (en) | 2012-01-24 |
| US20100076001A1 (en) | 2010-03-25 |
| ATE479680T1 (de) | 2010-09-15 |
| ES2349169T3 (es) | 2010-12-28 |
| EA200970615A1 (ru) | 2009-10-30 |
| JP5166441B2 (ja) | 2013-03-21 |
| KR101088291B1 (ko) | 2011-11-30 |
| AU2007334039A1 (en) | 2008-06-26 |
| WO2008076704A1 (en) | 2008-06-26 |
| AU2007334039B2 (en) | 2012-02-16 |
| DE602007008952D1 (de) | 2010-10-14 |
| BRPI0721045A2 (pt) | 2014-07-29 |
| JP2010513552A (ja) | 2010-04-30 |
| EP2125793B1 (en) | 2010-09-01 |
| MX2009006634A (es) | 2009-06-30 |
| EP2125793A1 (en) | 2009-12-02 |
| CA2671738A1 (en) | 2008-06-26 |
| KR20090086114A (ko) | 2009-08-10 |
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