MXPA02004366A - Derivados de quinazolina como inhibidores vegf. - Google Patents
Derivados de quinazolina como inhibidores vegf.Info
- Publication number
- MXPA02004366A MXPA02004366A MXPA02004366A MXPA02004366A MXPA02004366A MX PA02004366 A MXPA02004366 A MX PA02004366A MX PA02004366 A MXPA02004366 A MX PA02004366A MX PA02004366 A MXPA02004366 A MX PA02004366A MX PA02004366 A MXPA02004366 A MX PA02004366A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- methoxy
- quinazoline
- ylmethoxy
- compound
- Prior art date
Links
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract 2
- 239000002525 vasculotropin inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- -1 C1 4alkyl Chemical group 0.000 claims abstract description 119
- 150000003839 salts Chemical class 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 50
- 230000000694 effects Effects 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
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- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 32
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 230000008728 vascular permeability Effects 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 230000001772 anti-angiogenic effect Effects 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000003246 quinazolines Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004066 vascular targeting agent Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- PBESGEKOQIKSKI-UHFFFAOYSA-N n-(4-bromo-2,6-difluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC3CCNCC3)C(OC)=CC2=C1NC1=C(F)C=C(Br)C=C1F PBESGEKOQIKSKI-UHFFFAOYSA-N 0.000 claims description 2
- KQEHWOWUWGAOSR-UHFFFAOYSA-N n-(4-chloro-2,6-difluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC3CCN(C)CC3)C(OC)=CC2=C1NC1=C(F)C=C(Cl)C=C1F KQEHWOWUWGAOSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- KIWKXIDEBINNAK-UHFFFAOYSA-N n-(4-bromo-2,6-difluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC3CCN(C)CC3)C(OC)=CC2=C1NC1=C(F)C=C(Br)C=C1F KIWKXIDEBINNAK-UHFFFAOYSA-N 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99402759 | 1999-11-05 | ||
| EP99402877 | 1999-11-19 | ||
| PCT/GB2000/004181 WO2001032651A1 (en) | 1999-11-05 | 2000-11-01 | Quinazoline derivatives as vegf inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02004366A true MXPA02004366A (es) | 2002-11-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02004366A MXPA02004366A (es) | 1999-11-05 | 2000-11-01 | Derivados de quinazolina como inhibidores vegf. |
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