NL7906761A - Nieuwe 4-anilinochinazoline verbindingen en hun bereiding. - Google Patents
Nieuwe 4-anilinochinazoline verbindingen en hun bereiding. Download PDFInfo
- Publication number
- NL7906761A NL7906761A NL7906761A NL7906761A NL7906761A NL 7906761 A NL7906761 A NL 7906761A NL 7906761 A NL7906761 A NL 7906761A NL 7906761 A NL7906761 A NL 7906761A NL 7906761 A NL7906761 A NL 7906761A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- atom
- hydrogen atom
- compounds
- quinazoline
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 74
- 238000002360 preparation method Methods 0.000 title claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- -1 aniline compound Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 230000000202 analgesic effect Effects 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000730 antalgic agent Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 7
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229940035676 analgesics Drugs 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- NSCRIMVWSSNPQO-UHFFFAOYSA-N n-methyl-n-phenyl-7-(trifluoromethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC(C(F)(F)F)=CC=C2C=1N(C)C1=CC=CC=C1 NSCRIMVWSSNPQO-UHFFFAOYSA-N 0.000 claims description 2
- QQCFPFVGDZKUTF-UHFFFAOYSA-N n-phenyl-7-(trifluoromethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC(C(F)(F)F)=CC=C2C=1NC1=CC=CC=C1 QQCFPFVGDZKUTF-UHFFFAOYSA-N 0.000 claims description 2
- MTSNDBYBIZSILH-UHFFFAOYSA-N n-phenylquinazolin-4-amine Chemical class N=1C=NC2=CC=CC=C2C=1NC1=CC=CC=C1 MTSNDBYBIZSILH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
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- 239000000126 substance Substances 0.000 claims 1
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- 238000000354 decomposition reaction Methods 0.000 description 17
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- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
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- 238000000921 elemental analysis Methods 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000000460 chlorine Substances 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- FDPHWQSGEWRZOL-UHFFFAOYSA-N 4,7-dichloroquinazoline Chemical compound ClC1=NC=NC2=CC(Cl)=CC=C21 FDPHWQSGEWRZOL-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
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- IJNDITTYYNJLPT-UHFFFAOYSA-N 4-chloro-7-(trifluoromethyl)quinazoline Chemical compound ClC1=NC=NC2=CC(C(F)(F)F)=CC=C21 IJNDITTYYNJLPT-UHFFFAOYSA-N 0.000 description 2
- SLUNGDFHPGKYSO-UHFFFAOYSA-N 7-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC=NC2=CC(Cl)=CC=C12 SLUNGDFHPGKYSO-UHFFFAOYSA-N 0.000 description 2
- AQLFYKIRDFAQFS-UHFFFAOYSA-N 7-chloro-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=NC2=CC(Cl)=CC=C12 AQLFYKIRDFAQFS-UHFFFAOYSA-N 0.000 description 2
- WQTBXXKRJZOWDA-UHFFFAOYSA-N 8-chloro-n-phenylquinazolin-4-amine Chemical compound N1=CN=C2C(Cl)=CC=CC2=C1NC1=CC=CC=C1 WQTBXXKRJZOWDA-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 2
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- AHLKSOXEVRYIRD-UHFFFAOYSA-N n-phenylquinazolin-2-amine Chemical class N=1C=C2C=CC=CC2=NC=1NC1=CC=CC=C1 AHLKSOXEVRYIRD-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 230000003040 nociceptive effect Effects 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- VBUBADWLHFZFDK-UHFFFAOYSA-N quinazoline;hydrochloride Chemical compound Cl.N1=CN=CC2=CC=CC=C21 VBUBADWLHFZFDK-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11148478A JPS5538325A (en) | 1978-09-11 | 1978-09-11 | 4-anilinoquinazoline derivative and its preparation |
| JP11148478 | 1978-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7906761A true NL7906761A (nl) | 1980-03-13 |
Family
ID=14562420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7906761A NL7906761A (nl) | 1978-09-11 | 1979-09-11 | Nieuwe 4-anilinochinazoline verbindingen en hun bereiding. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4322420A (OSRAM) |
| JP (1) | JPS5538325A (OSRAM) |
| BE (1) | BE878723A (OSRAM) |
| CA (1) | CA1151168A (OSRAM) |
| CH (1) | CH642361A5 (OSRAM) |
| DE (1) | DE2936705A1 (OSRAM) |
| DK (1) | DK377079A (OSRAM) |
| ES (1) | ES484097A0 (OSRAM) |
| FR (1) | FR2435248A1 (OSRAM) |
| GB (1) | GB2033894B (OSRAM) |
| IT (1) | IT1119933B (OSRAM) |
| NL (1) | NL7906761A (OSRAM) |
| SE (1) | SE446337B (OSRAM) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5538325A (en) * | 1978-09-11 | 1980-03-17 | Sankyo Co Ltd | 4-anilinoquinazoline derivative and its preparation |
| JPS57144266A (en) * | 1981-03-04 | 1982-09-06 | Sankyo Co Ltd | 4-anilinoquinazoline derivative, its preparation, and analgesic and antiphlogistic agent containing said derivative as active component |
| JP2676082B2 (ja) * | 1987-12-25 | 1997-11-12 | 住友化学工業株式会社 | ゴキブリ防除用マイクロカプセル剤 |
| US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5710158A (en) * | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US6645969B1 (en) | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| DK0584222T3 (da) * | 1991-05-10 | 1998-02-23 | Rhone Poulenc Rorer Int | Bis-mono- og bicycliske aryl- og heteroarylforbindelser, som inhiberer EGF- og/eller PDGF-receptor-tyrosinkinase |
| US5714493A (en) * | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| USRE37650E1 (en) | 1991-05-10 | 2002-04-09 | Aventis Pharmacetical Products, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5733561A (en) * | 1991-06-12 | 1998-03-31 | Mitsui Toatsu Chemicals, Incorporated | Insecticide composition and production process thereof |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| US5234936A (en) * | 1991-10-24 | 1993-08-10 | American Home Products Corporation | Pyrimidocycloalkanes as a ii antagonists |
| AU661533B2 (en) * | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| ES2049659B1 (es) * | 1992-10-08 | 1994-10-16 | Ici Plc | Una composicion farmaceutica a base de derivados de quinazolina con actividad anti-cancerigena. |
| GB9314893D0 (en) * | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| AU739382B2 (en) * | 1993-12-10 | 2001-10-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US6214987B1 (en) | 1994-09-02 | 2001-04-10 | Andrew C. Hiatt | Compositions for enzyme catalyzed template-independent formation of phosphodiester bonds using protected nucleotides |
| US6232465B1 (en) | 1994-09-02 | 2001-05-15 | Andrew C. Hiatt | Compositions for enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides |
| TW321649B (OSRAM) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
| GB9424233D0 (en) * | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
| GB9508535D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivative |
| WO1996033977A1 (en) * | 1995-04-27 | 1996-10-31 | Zeneca Limited | Quinazoline derivatives |
| GB9508565D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9508537D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| PL194689B1 (pl) * | 1996-02-13 | 2007-06-29 | Astrazeneca Uk Ltd | Pochodne chinazoliny, ich kompozycje farmaceutyczne oraz ich zastosowania |
| GB9603097D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline compounds |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| EP0885198B1 (en) * | 1996-03-05 | 2001-12-19 | AstraZeneca AB | 4-anilinoquinazoline derivatives |
| GB9607729D0 (en) * | 1996-04-13 | 1996-06-19 | Zeneca Ltd | Quinazoline derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| US5939421A (en) * | 1997-07-01 | 1999-08-17 | Signal Pharmaceuticals, Inc. | Quinazoline analogs and related compounds and methods for treating inflammatory conditions |
| US6706721B1 (en) | 1998-04-29 | 2004-03-16 | Osi Pharmaceuticals, Inc. | N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate anhydrate and monohydrate |
| EP1082311A1 (en) | 1998-05-28 | 2001-03-14 | Parker Hughes Institute | Quinazolines for treating brain tumor |
| US6800649B1 (en) * | 1998-06-30 | 2004-10-05 | Parker Hughes Institute | Method for inhibiting c-jun expression using JAK-3 inhibitors |
| EP1105378B1 (en) * | 1998-08-21 | 2005-03-30 | Parker Hughes Institute | Quinazoline derivatives |
| US6080747A (en) | 1999-03-05 | 2000-06-27 | Hughes Institute | JAK-3 inhibitors for treating allergic disorders |
| US6258820B1 (en) | 1999-03-19 | 2001-07-10 | Parker Hughes Institute | Synthesis and anti-tumor activity of 6,7-dialkoxy-4-phenylamino-quinazolines |
| JP3522727B2 (ja) | 1999-11-05 | 2004-04-26 | アストラゼネカ アクチボラグ | Ｖｅｇｆ阻害剤としてのキナゾリン誘導体 |
| UA74803C2 (uk) | 1999-11-11 | 2006-02-15 | Осі Фармасьютікалз, Інк. | Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування |
| US7087613B2 (en) * | 1999-11-11 | 2006-08-08 | Osi Pharmaceuticals, Inc. | Treating abnormal cell growth with a stable polymorph of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride |
| DE60121931T2 (de) | 2000-04-07 | 2007-03-01 | Astrazeneca Ab | Chinazolinverbindungen |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| WO2003009815A2 (en) | 2001-07-25 | 2003-02-06 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| ATE423104T1 (de) * | 2001-11-03 | 2009-03-15 | Astrazeneca Ab | Quinazolin derivate als antitumor-mittel |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | Astrazeneca Ab | Quinazoline derivatives |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| KR101218213B1 (ko) * | 2003-07-03 | 2013-01-04 | 시토비아 인크. | 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| GB0317665D0 (en) | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026151A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| DE602004004553T2 (de) * | 2003-09-19 | 2007-10-25 | Astrazeneca Ab | Chinazolinderivate |
| EP1670782B1 (en) * | 2003-09-19 | 2007-02-14 | AstraZeneca AB | Quinazoline derivatives |
| EP1670786A1 (en) * | 2003-09-25 | 2006-06-21 | Astrazeneca AB | Quinazoline derivatives |
| WO2005042498A2 (en) * | 2003-10-31 | 2005-05-12 | Neurogen Corporation | 4-amino (aza) quinoline derivatives as capsaicin receptor agonists |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| US20070244114A1 (en) * | 2004-07-06 | 2007-10-18 | Myriad Genetics, Incorporated | Compounds and therapeutical use thereof |
| DE602005026865D1 (de) | 2004-12-14 | 2011-04-21 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8258145B2 (en) * | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| ATE521603T1 (de) | 2005-02-26 | 2011-09-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| US8847766B2 (en) | 2005-04-28 | 2014-09-30 | Proteus Digital Health, Inc. | Pharma-informatics system |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| EP1940825A1 (en) * | 2005-09-20 | 2008-07-09 | Astra Zeneca AB | Quinazoline derivatives as anticancer agents |
| EP1928861B1 (en) * | 2005-09-20 | 2010-11-17 | AstraZeneca AB | 4- (ih-indazol-5-yl-amino)-quinazoline compounds as erbb receptor tyrosine kinase inhibitors for the treatment of cancer |
| JP2009517450A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害薬としての４−アニリノ置換キナゾリン誘導体 |
| EP1960371B1 (en) * | 2005-12-02 | 2009-09-16 | AstraZeneca AB | Quinazoleine derivatives used as inhibitors of erbb tyrosine kinase |
| US20070231298A1 (en) * | 2006-03-31 | 2007-10-04 | Cell Genesys, Inc. | Cytokine-expressing cancer immunotherapy combinations |
| WO2008009078A2 (en) * | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| US8246966B2 (en) * | 2006-08-07 | 2012-08-21 | University Of Georgia Research Foundation, Inc. | Trypanosome microsome system and uses thereof |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| WO2008066755A2 (en) * | 2006-11-22 | 2008-06-05 | University Of Georgia Research Foundation, Inc. | Tyrosine kinase inhibitors as anti-kinetolastid and anti-apicomplexan agents |
| AU2008212999A1 (en) | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| EP2245026B1 (de) | 2008-02-07 | 2012-08-01 | Boehringer Ingelheim International GmbH | Spirocyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| AU2009247782C1 (en) | 2008-05-13 | 2013-09-19 | Astrazeneca Ab | Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- { [1- (N-methylcarbamoylmethyl) piperidin- 4-yl] oxy } quinazoline |
| CA2733153C (en) | 2008-08-08 | 2016-11-08 | Boehringer Ingelheim International Gmbh | Cyclohexyloxy substituted heterocycles, pharmaceutical compositions containing these compounds and processes for preparing them |
| EP2398500B1 (en) | 2009-02-20 | 2019-03-13 | 2-BBB Medicines B.V. | Glutathione-based drug delivery system |
| BRPI1011188B1 (pt) | 2009-05-06 | 2019-10-15 | Laboratory Skin Care, Inc. | Composições de liberação dérmica compreendendo complexos de partículas de agente ativo-fosfato de cálcio e métodos para usar as mesmas |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| CN110372666B (zh) * | 2018-04-13 | 2022-11-08 | 华东理工大学 | 喹唑啉类化合物作为egfr三突变抑制剂及其应用 |
| CN113811528A (zh) | 2019-03-15 | 2021-12-17 | 加利福尼亚大学董事会 | 用于治疗癌症的组合物和方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1724086A (en) * | 1929-08-13 | Eentrich astd max hardtmankt | ||
| US2794018A (en) * | 1953-08-07 | 1957-05-28 | New quinazoline derivatives | |
| CH492395A (de) * | 1966-04-26 | 1970-06-30 | Sandoz Ag | Mittel zur Bekämpfung von Pflanzenschädlingen und Verwendung des Mittels |
| US3560619A (en) * | 1967-01-03 | 1971-02-02 | Mead Johnson & Co | Aminoquinazolines and quinazolones in treatment of coccidiosis |
| US3702849A (en) * | 1967-10-26 | 1972-11-14 | Pfizer | 4-(isoquinolin-1-yl) piperazine-1-carboxylic acid esters |
| US4041030A (en) * | 1973-09-20 | 1977-08-09 | Delalande S.A. | Arylamino pyrimidinic derivatives |
| US3985749A (en) * | 1975-12-22 | 1976-10-12 | Eastman Kodak Company | Process for preparation of 4-aminoquinazoline |
| JPS5538325A (en) * | 1978-09-11 | 1980-03-17 | Sankyo Co Ltd | 4-anilinoquinazoline derivative and its preparation |
-
1978
- 1978-09-11 JP JP11148478A patent/JPS5538325A/ja active Granted
-
1979
- 1979-09-10 SE SE7907493A patent/SE446337B/sv unknown
- 1979-09-10 IT IT68794/79A patent/IT1119933B/it active
- 1979-09-10 CH CH816679A patent/CH642361A5/de not_active IP Right Cessation
- 1979-09-10 CA CA000335246A patent/CA1151168A/en not_active Expired
- 1979-09-10 DK DK377079A patent/DK377079A/da unknown
- 1979-09-11 BE BE0/197102A patent/BE878723A/fr not_active IP Right Cessation
- 1979-09-11 FR FR7922639A patent/FR2435248A1/fr active Granted
- 1979-09-11 US US06/074,343 patent/US4322420A/en not_active Expired - Lifetime
- 1979-09-11 DE DE19792936705 patent/DE2936705A1/de not_active Withdrawn
- 1979-09-11 NL NL7906761A patent/NL7906761A/nl not_active Application Discontinuation
- 1979-09-11 GB GB7931441A patent/GB2033894B/en not_active Expired
- 1979-09-11 ES ES484097A patent/ES484097A0/es active Granted
-
1981
- 1981-08-03 US US06/289,379 patent/US4464375A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2033894A (en) | 1980-05-29 |
| JPS5538325A (en) | 1980-03-17 |
| JPS626546B2 (OSRAM) | 1987-02-12 |
| US4322420A (en) | 1982-03-30 |
| IT1119933B (it) | 1986-03-19 |
| FR2435248A1 (fr) | 1980-04-04 |
| GB2033894B (en) | 1983-02-16 |
| US4464375A (en) | 1984-08-07 |
| DK377079A (da) | 1980-03-12 |
| BE878723A (fr) | 1980-03-11 |
| CH642361A5 (de) | 1984-04-13 |
| CA1151168A (en) | 1983-08-02 |
| IT7968794A0 (it) | 1979-09-10 |
| DE2936705A1 (de) | 1980-03-20 |
| ES8100276A1 (es) | 1980-11-01 |
| ES484097A0 (es) | 1980-11-01 |
| SE446337B (sv) | 1986-09-01 |
| FR2435248B1 (OSRAM) | 1983-02-18 |
| SE7907493L (sv) | 1980-03-12 |
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