ZA200402054B - Processes for the preparation of substituted bicyclic derivatives for the treatment of abnormal cell growth. - Google Patents
Processes for the preparation of substituted bicyclic derivatives for the treatment of abnormal cell growth. Download PDFInfo
- Publication number
- ZA200402054B ZA200402054B ZA200402054A ZA200402054A ZA200402054B ZA 200402054 B ZA200402054 B ZA 200402054B ZA 200402054 A ZA200402054 A ZA 200402054A ZA 200402054 A ZA200402054 A ZA 200402054A ZA 200402054 B ZA200402054 B ZA 200402054B
- Authority
- ZA
- South Africa
- Prior art keywords
- integer
- alkyl
- aryl
- optionally substituted
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 125000002619 bicyclic group Chemical group 0.000 title claims description 7
- 230000008569 process Effects 0.000 title description 18
- 230000002159 abnormal effect Effects 0.000 title description 5
- 230000010261 cell growth Effects 0.000 title description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 41
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- -1 -NR'R? Chemical group 0.000 claims description 24
- 125000004434 sulfur atom Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims description 2
- CAAQAOPBTSEEPE-UHFFFAOYSA-N 2-(hydroxymethyl)pyrrolidine-1-carboxylic acid Chemical compound OCC1CCCN1C(O)=O CAAQAOPBTSEEPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 claims 3
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims 3
- AFNJRWJHTHPHFY-UHFFFAOYSA-N 2-(dimethylamino)-n-[3-[4-(3-methyl-4-pyridin-3-yloxyanilino)quinazolin-6-yl]prop-2-ynyl]acetamide Chemical compound C12=CC(C#CCNC(=O)CN(C)C)=CC=C2N=CN=C1NC(C=C1C)=CC=C1OC1=CC=CN=C1 AFNJRWJHTHPHFY-UHFFFAOYSA-N 0.000 claims 1
- ZYAJQMUTJUFTQJ-UHFFFAOYSA-N 2-methoxy-n-[1-[2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]ethynyl]cyclopropyl]acetamide Chemical compound C=1C=C2N=CN=C(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)C2=CC=1C#CC1(NC(=O)COC)CC1 ZYAJQMUTJUFTQJ-UHFFFAOYSA-N 0.000 claims 1
- 229910014585 C2-Ce Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- PGNQYDWBJQHLKF-UHFFFAOYSA-N n-[3-[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]prop-2-ynyl]acetamide Chemical compound C12=CC(C#CCNC(=O)C)=CC=C2N=CN=C1NC(C=C1Cl)=CC=C1OC1=CC=C(C)N=C1 PGNQYDWBJQHLKF-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 102000001301 EGF receptor Human genes 0.000 description 5
- 108060006698 EGF receptor Proteins 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 5
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 3
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 108700020796 Oncogene Proteins 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 229940124639 Selective inhibitor Drugs 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- BAVGSGLGSGTNSC-UHFFFAOYSA-N 2-methoxy-n-[3-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]prop-2-ynyl]acetamide Chemical compound C12=CC(C#CCNC(=O)COC)=CC=C2N=CN=C1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 BAVGSGLGSGTNSC-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 125000006549 C4-C10 aryl group Chemical group 0.000 description 1
- 108091007914 CDKs Proteins 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- 101100481408 Danio rerio tie2 gene Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- 208000009849 Female Genital Neoplasms Diseases 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 101100481410 Mus musculus Tek gene Proteins 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 102000043276 Oncogene Human genes 0.000 description 1
- 102000016979 Other receptors Human genes 0.000 description 1
- 101150093908 PDGFRB gene Proteins 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 108091008605 VEGF receptors Proteins 0.000 description 1
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000011717 athymic nude mouse Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000010307 cell transformation Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- SIHZWGODIRRSRA-ONEGZZNKSA-N erbstatin Chemical compound OC1=CC=C(O)C(\C=C\NC=O)=C1 SIHZWGODIRRSRA-ONEGZZNKSA-N 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NUXRNLPBHAIASC-UHFFFAOYSA-N n-(3-methyl-4-pyridin-3-yloxyphenyl)-6-(2-piperidin-4-ylethynyl)quinazolin-4-amine Chemical compound C=1C=C(OC=2C=NC=CC=2)C(C)=CC=1NC(C1=C2)=NC=NC1=CC=C2C#CC1CCNCC1 NUXRNLPBHAIASC-UHFFFAOYSA-N 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 208000013076 thyroid tumor Diseases 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
Classifications
-
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33464701P | 2001-11-30 | 2001-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200402054B true ZA200402054B (en) | 2005-05-23 |
Family
ID=23308141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200402054A ZA200402054B (en) | 2001-11-30 | 2004-03-15 | Processes for the preparation of substituted bicyclic derivatives for the treatment of abnormal cell growth. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20030144506A1 (hu) |
| EP (1) | EP1448551B1 (hu) |
| JP (1) | JP4220388B2 (hu) |
| KR (1) | KR20040054813A (hu) |
| CN (1) | CN1639149A (hu) |
| AR (1) | AR037591A1 (hu) |
| AT (1) | ATE377009T1 (hu) |
| AU (1) | AU2002337428A1 (hu) |
| BR (1) | BR0214606A (hu) |
| CA (1) | CA2462149C (hu) |
| DE (1) | DE60223279T2 (hu) |
| DO (1) | DOP2002000519A (hu) |
| ES (1) | ES2295409T3 (hu) |
| GT (1) | GT200200245A (hu) |
| HN (1) | HN2002000334A (hu) |
| HU (1) | HUP0500117A3 (hu) |
| IL (1) | IL160971A0 (hu) |
| MX (1) | MXPA04005157A (hu) |
| PA (1) | PA8558601A1 (hu) |
| PE (1) | PE20030643A1 (hu) |
| PL (1) | PL370911A1 (hu) |
| RS (1) | RS44004A (hu) |
| RU (1) | RU2004116345A (hu) |
| SV (1) | SV2004001419A (hu) |
| TN (1) | TNSN02096A1 (hu) |
| TW (1) | TW200300691A (hu) |
| WO (1) | WO2003045939A1 (hu) |
| ZA (1) | ZA200402054B (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2510323A1 (en) * | 2002-12-18 | 2004-07-01 | Pfizer Products Inc. | 4-anilino quinazoline derivatives for the treatment of abnormal cell growth |
| PL377533A1 (pl) * | 2002-12-19 | 2006-02-06 | Pfizer Products Inc. | Kompleksy E-2-metoksy-N-(3-{4-[3-metylo-4-(6-metylopirydyn-3-yloksy)-fenyloamino]-chinazolin-6-ylo}-allilo)-acetamidu, sposób ich wytwarzania i zastosowanie |
| AU2004228460A1 (en) * | 2003-04-09 | 2004-10-21 | Pfizer Products Inc. | Processes for the preparation of N-((((pyridinyloxy) -phenylamino) quinazolinyl)- allyl) acetamide derivatives and related compounds as well as intermediates of such processes and processes for the preparation of such intermediates |
| WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| NZ544472A (en) * | 2003-07-03 | 2009-04-30 | Myriad Genetics Inc | Compounds and therapeutical use thereof |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| US20050192298A1 (en) * | 2004-02-27 | 2005-09-01 | Pfizer Inc | Crystal forms of E-2-Methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-acetamide |
| CA2565812C (en) * | 2004-05-06 | 2012-03-13 | Warner-Lambert Company Llc | 4-phenylamino-quinazolin-6-yl-amides |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| WO2007072499A2 (en) * | 2005-12-02 | 2007-06-28 | The Paper Products Limited | Holographic flexible tube laminate for packaging and method of making the same |
| BR112021005513A2 (pt) | 2018-09-25 | 2021-06-22 | Black Diamond Therapeutics, Inc. | derivados de quinazolina como inibidor de tirosina quinase, composições, métodos de fabricação e uso dos mesmos |
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|---|---|---|---|---|
| TW321649B (hu) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
| DE19501481A1 (de) * | 1995-01-19 | 1996-07-25 | Bayer Ag | 2,8-Disubstituierte Chinazolinone |
| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| CZ20023951A3 (cs) * | 2000-06-22 | 2004-01-14 | Pfizer Products Inc. | Substituované bicyklické deriváty pro léčení abnormálního buničného růstu |
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2002
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- 2002-10-03 AT AT02772689T patent/ATE377009T1/de not_active IP Right Cessation
- 2002-10-03 CN CNA028208994A patent/CN1639149A/zh active Pending
- 2002-10-03 WO PCT/IB2002/004097 patent/WO2003045939A1/en active IP Right Grant
- 2002-10-03 AU AU2002337428A patent/AU2002337428A1/en not_active Abandoned
- 2002-10-03 BR BR0214606-1A patent/BR0214606A/pt not_active IP Right Cessation
- 2002-10-03 DE DE60223279T patent/DE60223279T2/de not_active Expired - Lifetime
- 2002-10-03 EP EP02772689A patent/EP1448551B1/en not_active Expired - Lifetime
- 2002-10-03 ES ES02772689T patent/ES2295409T3/es not_active Expired - Lifetime
- 2002-10-03 IL IL16097102A patent/IL160971A0/xx unknown
- 2002-10-03 RS YU44004A patent/RS44004A/sr unknown
- 2002-10-03 KR KR10-2004-7008290A patent/KR20040054813A/ko not_active Application Discontinuation
- 2002-10-03 HU HU0500117A patent/HUP0500117A3/hu unknown
- 2002-10-03 CA CA2462149A patent/CA2462149C/en not_active Expired - Fee Related
- 2002-10-03 PL PL02370911A patent/PL370911A1/xx unknown
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- 2002-10-03 JP JP2003547389A patent/JP4220388B2/ja not_active Expired - Fee Related
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- 2002-11-25 PA PA20028558601A patent/PA8558601A1/es unknown
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- 2002-11-28 AR ARP020104590A patent/AR037591A1/es unknown
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- 2002-12-02 US US10/307,603 patent/US20030144506A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| TW200300691A (en) | 2003-06-16 |
| JP4220388B2 (ja) | 2009-02-04 |
| KR20040054813A (ko) | 2004-06-25 |
| ES2295409T3 (es) | 2008-04-16 |
| PA8558601A1 (es) | 2003-06-30 |
| CN1639149A (zh) | 2005-07-13 |
| JP2005515986A (ja) | 2005-06-02 |
| DE60223279D1 (de) | 2007-12-13 |
| BR0214606A (pt) | 2004-09-14 |
| DOP2002000519A (es) | 2003-05-31 |
| PE20030643A1 (es) | 2003-07-23 |
| AR037591A1 (es) | 2004-11-17 |
| EP1448551B1 (en) | 2007-10-31 |
| TNSN02096A1 (en) | 2005-12-23 |
| HUP0500117A2 (hu) | 2005-05-30 |
| HN2002000334A (es) | 2003-02-21 |
| RS44004A (en) | 2006-10-27 |
| MXPA04005157A (es) | 2004-08-11 |
| SV2004001419A (es) | 2004-02-24 |
| CA2462149C (en) | 2010-06-22 |
| AU2002337428A1 (en) | 2003-06-10 |
| ATE377009T1 (de) | 2007-11-15 |
| CA2462149A1 (en) | 2003-06-05 |
| EP1448551A1 (en) | 2004-08-25 |
| RU2004116345A (ru) | 2005-03-27 |
| DE60223279T2 (de) | 2008-05-29 |
| WO2003045939A1 (en) | 2003-06-05 |
| PL370911A1 (en) | 2005-05-30 |
| US20030144506A1 (en) | 2003-07-31 |
| IL160971A0 (en) | 2004-08-31 |
| GT200200245A (es) | 2003-09-24 |
| HUP0500117A3 (en) | 2008-03-28 |
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