ZA200602191B - Quinazoline derivatives as tyrosine kinase inhibitors - Google Patents
Quinazoline derivatives as tyrosine kinase inhibitors Download PDFInfo
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- ZA200602191B ZA200602191B ZA200602191A ZA200602191A ZA200602191B ZA 200602191 B ZA200602191 B ZA 200602191B ZA 200602191 A ZA200602191 A ZA 200602191A ZA 200602191 A ZA200602191 A ZA 200602191A ZA 200602191 B ZA200602191 B ZA 200602191B
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- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- alkoxy
- formula
- hydroxy
- Prior art date
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- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title claims description 11
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 4
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 734
- -1 carboxy, carbamoyl Chemical group 0.000 claims description 499
- 125000003545 alkoxy group Chemical group 0.000 claims description 310
- 125000001424 substituent group Chemical group 0.000 claims description 199
- 125000000623 heterocyclic group Chemical group 0.000 claims description 147
- 125000003282 alkyl amino group Chemical group 0.000 claims description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 239000001257 hydrogen Substances 0.000 claims description 103
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 150000003246 quinazolines Chemical class 0.000 claims description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 71
- 150000002148 esters Chemical class 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000001153 fluoro group Chemical group F* 0.000 claims description 55
- 125000001589 carboacyl group Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 41
- 125000000304 alkynyl group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 33
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 30
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- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 125000004423 acyloxy group Chemical group 0.000 claims description 26
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 26
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 23
- 125000003386 piperidinyl group Chemical group 0.000 claims description 22
- 125000001246 bromo group Chemical group Br* 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 19
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 19
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
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- 201000011510 cancer Diseases 0.000 claims description 16
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 16
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
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- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 13
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003551 oxepanyl group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
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- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 7
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 6
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- BBWHNPBFCSESKS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(2-methoxyethoxy)ethanone Chemical compound C1CN(C(=O)COCCOC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC BBWHNPBFCSESKS-UHFFFAOYSA-N 0.000 claims description 2
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- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 2
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- GKAQAIGUPWXDDZ-AWEZNQCLSA-N (2s)-1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-methoxypropan-1-one Chemical compound C1CN(C(=O)[C@H](C)OC)CCC1OC1=CC2=NC=NC(NC=3C(=C(Cl)C=CC=3)F)=C2C=C1OC GKAQAIGUPWXDDZ-AWEZNQCLSA-N 0.000 claims 1
- PZZCHOWGOUUGLJ-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(4-methylpiperazin-1-yl)ethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CN3CCN(C)CC3)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F PZZCHOWGOUUGLJ-UHFFFAOYSA-N 0.000 claims 1
- MZVZZNYVRCEGDS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F MZVZZNYVRCEGDS-UHFFFAOYSA-N 0.000 claims 1
- ZWEKFSQMEWHVMO-UHFFFAOYSA-N 1-[4-[4-(3-chloro-2-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypiperidin-1-yl]-3-hydroxypropan-1-one Chemical compound N1=CN=C2C=C(OC3CCN(CC3)C(=O)CCO)C(OC)=CC2=C1NC1=CC=CC(Cl)=C1F ZWEKFSQMEWHVMO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0321620.7A GB0321620D0 (en) | 2003-09-16 | 2003-09-16 | Quinazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200602191B true ZA200602191B (en) | 2007-07-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200602191A ZA200602191B (en) | 2003-09-16 | 2006-03-15 | Quinazoline derivatives as tyrosine kinase inhibitors |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR101244524B1 (ko) |
| CN (1) | CN1882567B (ko) |
| GB (1) | GB0321620D0 (ko) |
| ZA (1) | ZA200602191B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102452988B (zh) | 2010-10-27 | 2016-01-27 | 中国科学院化学研究所 | 一种喹唑啉衍生物及其制备方法 |
| AR092529A1 (es) * | 2012-09-13 | 2015-04-22 | Glaxosmithkline Llc | Compuesto de aminoquinazolina, composicion farmaceutica que lo comprende y uso de dicho compuesto para la preparacion de un medicamento |
| TWI567063B (zh) * | 2014-09-05 | 2017-01-21 | 國立交通大學 | 用於促進癌細胞凋亡的化合物、其醫藥組成物及其用途 |
| CN108078990B (zh) * | 2016-11-23 | 2023-06-02 | 山东轩竹医药科技有限公司 | 喹唑啉衍生物类酪氨酸激酶抑制剂的新用途 |
| UY37935A (es) * | 2017-10-18 | 2020-03-31 | Spectrum Pharmaceuticals Inc | Inhibidores de tirosina quinasas de la familia de los egfr mutantes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6344455B1 (en) * | 1998-11-19 | 2002-02-05 | Warner-Lambert Company | N-[4-(3-chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide, and irreversible inhibitor of tyrosine kinases |
| WO2002092578A1 (en) * | 2001-05-14 | 2002-11-21 | Astrazeneca Ab | Quinazoline derivatives |
-
2003
- 2003-09-16 GB GBGB0321620.7A patent/GB0321620D0/en not_active Ceased
-
2004
- 2004-09-13 KR KR1020067007266A patent/KR101244524B1/ko not_active IP Right Cessation
- 2004-09-13 CN CN200480033525XA patent/CN1882567B/zh not_active Expired - Fee Related
-
2006
- 2006-03-15 ZA ZA200602191A patent/ZA200602191B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB0321620D0 (en) | 2003-10-15 |
| CN1882567A (zh) | 2006-12-20 |
| KR20070023631A (ko) | 2007-02-28 |
| KR101244524B1 (ko) | 2013-03-19 |
| CN1882567B (zh) | 2010-12-15 |
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