RU2350618C2 - ПРОИЗВОДНЫЕ ХИНАЗОЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ Src ТИРОЗИНКИНАЗЫ - Google Patents
ПРОИЗВОДНЫЕ ХИНАЗОЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ Src ТИРОЗИНКИНАЗЫ Download PDFInfo
- Publication number
- RU2350618C2 RU2350618C2 RU2005117337/04A RU2005117337A RU2350618C2 RU 2350618 C2 RU2350618 C2 RU 2350618C2 RU 2005117337/04 A RU2005117337/04 A RU 2005117337/04A RU 2005117337 A RU2005117337 A RU 2005117337A RU 2350618 C2 RU2350618 C2 RU 2350618C2
- Authority
- RU
- Russia
- Prior art keywords
- ethoxy
- propoxy
- group
- piperazin
- chloro
- Prior art date
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims 2
- 102000009076 src-Family Kinases Human genes 0.000 title 1
- 108010087686 src-Family Kinases Proteins 0.000 title 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
- -1 tetrahydropyran-4-yloxy Chemical group 0.000 claims abstract 40
- 150000003839 salts Chemical class 0.000 claims abstract 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 7
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims abstract 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract 5
- 230000001740 anti-invasion Effects 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 4
- 239000003085 diluting agent Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims abstract 2
- 150000003246 quinazolines Chemical class 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims 3
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims 3
- XQGNSUGMUSXKKB-UHFFFAOYSA-N 1-[4-[2-[4-[(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-yl)amino]-5-(oxan-4-yloxy)quinazolin-7-yl]oxyethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=CC(OC2CCOCC2)=C(C(NC=2C(=CN=C3OCOC3=2)Cl)=NC=N2)C2=C1 XQGNSUGMUSXKKB-UHFFFAOYSA-N 0.000 claims 1
- CETXQBFLIVLDTF-UHFFFAOYSA-N 1-[4-[2-[4-[(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-yl)amino]-5-propan-2-yloxyquinazolin-7-yl]oxyethyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCN(C(=O)CN(C)C)CC1 CETXQBFLIVLDTF-UHFFFAOYSA-N 0.000 claims 1
- MVWATCATLSSVBH-UHFFFAOYSA-N 1-[4-[2-[4-[(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-yl)amino]-5-propan-2-yloxyquinazolin-7-yl]oxyethyl]piperazin-1-yl]ethanone Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCN(C(C)=O)CC1 MVWATCATLSSVBH-UHFFFAOYSA-N 0.000 claims 1
- XACGJHGLWHFNKU-UHFFFAOYSA-N 2-[4-[2-[4-[(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-yl)amino]-5-propan-2-yloxyquinazolin-7-yl]oxyethyl]piperazin-1-yl]ethanol Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCN(CCO)CC1 XACGJHGLWHFNKU-UHFFFAOYSA-N 0.000 claims 1
- SDYDJNLCQKFKIL-UHFFFAOYSA-N 6-chloro-n-[5-(oxan-4-yloxy)-7-[2-(4-prop-2-ynylpiperazin-1-yl)ethoxy]quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2OCOC2=C1NC(C1=C(OC2CCOCC2)C=2)=NC=NC1=CC=2OCCN1CCN(CC#C)CC1 SDYDJNLCQKFKIL-UHFFFAOYSA-N 0.000 claims 1
- ZBQDUFLGPNBYCE-UHFFFAOYSA-N 6-chloro-n-[5-(oxan-4-yloxy)-7-[3-(4-prop-2-ynylpiperazin-1-yl)propoxy]quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2OCOC2=C1NC(C1=C(OC2CCOCC2)C=2)=NC=NC1=CC=2OCCCN1CCN(CC#C)CC1 ZBQDUFLGPNBYCE-UHFFFAOYSA-N 0.000 claims 1
- FJNMDDYFEUEVLJ-UHFFFAOYSA-N 6-chloro-n-[5-propan-2-yloxy-7-(2-pyrrolidin-1-ylethoxy)quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCCC1 FJNMDDYFEUEVLJ-UHFFFAOYSA-N 0.000 claims 1
- AMXMRGRLUQUEDG-UHFFFAOYSA-N 6-chloro-n-[5-propan-2-yloxy-7-[2-(4-prop-2-ynylpiperazin-1-yl)ethoxy]quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCN(CC#C)CC1 AMXMRGRLUQUEDG-UHFFFAOYSA-N 0.000 claims 1
- LHNUBGOLVVVBFV-UHFFFAOYSA-N 6-chloro-n-[7-(2-morpholin-4-ylethoxy)-5-(oxan-4-yloxy)quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2OCOC2=C1NC(C1=C(OC2CCOCC2)C=2)=NC=NC1=CC=2OCCN1CCOCC1 LHNUBGOLVVVBFV-UHFFFAOYSA-N 0.000 claims 1
- CIYSACKPZCOGHC-UHFFFAOYSA-N 6-chloro-n-[7-(2-morpholin-4-ylethoxy)-5-propan-2-yloxyquinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCOCC1 CIYSACKPZCOGHC-UHFFFAOYSA-N 0.000 claims 1
- LXWLEHANZSZKOO-UHFFFAOYSA-N 6-chloro-n-[7-(2-piperazin-1-ylethoxy)-5-propan-2-yloxyquinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCNCC1 LXWLEHANZSZKOO-UHFFFAOYSA-N 0.000 claims 1
- CMSYDWDIPDBPGZ-UHFFFAOYSA-N 6-chloro-n-[7-(2-piperidin-1-ylethoxy)-5-propan-2-yloxyquinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCCCC1 CMSYDWDIPDBPGZ-UHFFFAOYSA-N 0.000 claims 1
- STMAOZDCKQKDGH-UHFFFAOYSA-N 6-chloro-n-[7-(3-morpholin-4-ylpropoxy)-5-(oxan-4-yloxy)quinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2OCOC2=C1NC(C1=C(OC2CCOCC2)C=2)=NC=NC1=CC=2OCCCN1CCOCC1 STMAOZDCKQKDGH-UHFFFAOYSA-N 0.000 claims 1
- QOCFWLMWEMNAJO-UHFFFAOYSA-N 6-chloro-n-[7-(3-morpholin-4-ylpropoxy)-5-propan-2-yloxyquinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCCN1CCOCC1 QOCFWLMWEMNAJO-UHFFFAOYSA-N 0.000 claims 1
- NPLQFGONSPDLQX-UHFFFAOYSA-N 6-chloro-n-[7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-propan-2-yloxyquinazolin-4-yl]-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound C=1C2=NC=NC(NC=3C(=CN=C4OCOC4=3)Cl)=C2C(OC(C)C)=CC=1OCCN1CCN(C)CC1 NPLQFGONSPDLQX-UHFFFAOYSA-N 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- DANWDGOLHZFHLA-UHFFFAOYSA-N n-[7-[2-(3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)ethoxy]-5-(oxan-4-yloxy)quinazolin-4-yl]-6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2OCOC2=C1NC(C=12)=NC=NC2=CC(OCCN2CC3OCOC3C2)=CC=1OC1CCOCC1 DANWDGOLHZFHLA-UHFFFAOYSA-N 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 4
- 201000011510 cancer Diseases 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
- 102000001253 Protein Kinase Human genes 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 108060006633 protein kinase Proteins 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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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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- 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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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02292736 | 2002-11-04 | ||
| EP02292736.2 | 2002-11-04 | ||
| EP03290900.4 | 2003-04-10 | ||
| EP03290900 | 2003-04-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005117337A RU2005117337A (ru) | 2006-01-20 |
| RU2350618C2 true RU2350618C2 (ru) | 2009-03-27 |
Family
ID=32313852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005117337/04A RU2350618C2 (ru) | 2002-11-04 | 2003-10-29 | ПРОИЗВОДНЫЕ ХИНАЗОЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ Src ТИРОЗИНКИНАЗЫ |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7462623B2 (enExample) |
| EP (1) | EP1562955B1 (enExample) |
| JP (2) | JP4593464B2 (enExample) |
| KR (1) | KR101089462B1 (enExample) |
| AR (1) | AR041884A1 (enExample) |
| AT (1) | ATE387451T1 (enExample) |
| AU (1) | AU2003278383B2 (enExample) |
| BR (1) | BR0315756A (enExample) |
| CA (1) | CA2503371C (enExample) |
| CO (1) | CO5560578A2 (enExample) |
| CY (1) | CY1108061T1 (enExample) |
| DE (1) | DE60319410T2 (enExample) |
| DK (1) | DK1562955T3 (enExample) |
| EG (1) | EG24957A (enExample) |
| ES (1) | ES2300619T3 (enExample) |
| IL (1) | IL168013A (enExample) |
| IS (1) | IS2568B (enExample) |
| MX (1) | MXPA05004858A (enExample) |
| MY (1) | MY137835A (enExample) |
| NO (1) | NO331951B1 (enExample) |
| NZ (1) | NZ539408A (enExample) |
| PL (1) | PL215161B1 (enExample) |
| PT (1) | PT1562955E (enExample) |
| RU (1) | RU2350618C2 (enExample) |
| SI (1) | SI1562955T1 (enExample) |
| TW (1) | TWI320786B (enExample) |
| WO (1) | WO2004041829A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2491191C (en) | 2002-07-15 | 2014-02-04 | Exelixis, Inc. | Receptor-type kinase modulators and methods of use |
| CA2744997A1 (en) | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and method of use |
| GB0406445D0 (en) * | 2004-03-23 | 2004-04-28 | Astrazeneca Ab | Combination therapy |
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