AU783116B2 - NSAID and EFGR kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer - Google Patents
NSAID and EFGR kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer Download PDFInfo
- Publication number
- AU783116B2 AU783116B2 AU63959/00A AU6395900A AU783116B2 AU 783116 B2 AU783116 B2 AU 783116B2 AU 63959/00 A AU63959/00 A AU 63959/00A AU 6395900 A AU6395900 A AU 6395900A AU 783116 B2 AU783116 B2 AU 783116B2
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- AU
- Australia
- Prior art keywords
- carbon atoms
- alkyl
- carbon
- phenyl
- substituted
- Prior art date
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- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 title claims description 77
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 title claims description 77
- 206010009944 Colon cancer Diseases 0.000 title claims description 15
- 208000035984 Colonic Polyps Diseases 0.000 title claims description 15
- 208000001333 Colorectal Neoplasms Diseases 0.000 title claims description 14
- 230000005764 inhibitory process Effects 0.000 title claims description 14
- 229940043355 kinase inhibitor Drugs 0.000 title description 14
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 14
- 239000000203 mixture Substances 0.000 title description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 1502
- -1 ketoporfen Chemical compound 0.000 claims description 390
- 125000000217 alkyl group Chemical group 0.000 claims description 169
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 229910052799 carbon Inorganic materials 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 90
- 125000000304 alkynyl group Chemical group 0.000 claims description 86
- 229940121647 egfr inhibitor Drugs 0.000 claims description 86
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 84
- 150000002431 hydrogen Chemical class 0.000 claims description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 150000002367 halogens Chemical group 0.000 claims description 65
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 63
- 150000003254 radicals Chemical class 0.000 claims description 63
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- 125000004970 halomethyl group Chemical group 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 150000001721 carbon Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 42
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 42
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 42
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 41
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004076 pyridyl group Chemical group 0.000 claims description 38
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 37
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
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- 238000000034 method Methods 0.000 claims description 34
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 33
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims description 31
- 229960000894 sulindac Drugs 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
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- 125000004423 acyloxy group Chemical group 0.000 claims description 24
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 23
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 19
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 19
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 18
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 16
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 12
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 11
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229930192474 thiophene Natural products 0.000 claims description 11
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 10
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
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- 230000002401 inhibitory effect Effects 0.000 claims description 6
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- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims description 3
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- 229940102223 injectable solution Drugs 0.000 description 1
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- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
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- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical class N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NRTUTGBOQZQBMB-UHFFFAOYSA-N n-phenylquinolin-4-amine Chemical class C=1C=NC2=CC=CC=C2C=1NC1=CC=CC=C1 NRTUTGBOQZQBMB-UHFFFAOYSA-N 0.000 description 1
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- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
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- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000021014 regulation of cell growth Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37326199A | 1999-08-12 | 1999-08-12 | |
| US09/373261 | 1999-08-12 | ||
| PCT/US2000/021021 WO2001012227A1 (en) | 1999-08-12 | 2000-08-02 | Nsaid and efgr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6395900A AU6395900A (en) | 2001-03-13 |
| AU783116B2 true AU783116B2 (en) | 2005-09-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU63959/00A Ceased AU783116B2 (en) | 1999-08-12 | 2000-08-02 | NSAID and EFGR kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
Country Status (24)
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|---|---|
| EP (1) | EP1202746B1 (enExample) |
| JP (1) | JP2003507342A (enExample) |
| KR (1) | KR20020018201A (enExample) |
| CN (1) | CN1229142C (enExample) |
| AR (1) | AR029763A1 (enExample) |
| AT (1) | ATE341341T1 (enExample) |
| AU (1) | AU783116B2 (enExample) |
| BR (1) | BR0013219A (enExample) |
| CA (1) | CA2380904C (enExample) |
| CZ (1) | CZ2002474A3 (enExample) |
| DE (1) | DE60031127T2 (enExample) |
| DK (1) | DK1202746T3 (enExample) |
| EA (1) | EA006876B1 (enExample) |
| ES (1) | ES2272305T3 (enExample) |
| HK (1) | HK1042244A1 (enExample) |
| HU (1) | HUP0203162A3 (enExample) |
| IL (1) | IL147913A0 (enExample) |
| MX (1) | MXPA02001448A (enExample) |
| NO (1) | NO20020663L (enExample) |
| NZ (1) | NZ517120A (enExample) |
| PL (1) | PL353267A1 (enExample) |
| PT (1) | PT1202746E (enExample) |
| WO (1) | WO2001012227A1 (enExample) |
| ZA (1) | ZA200201156B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040127470A1 (en) * | 1998-12-23 | 2004-07-01 | Pharmacia Corporation | Methods and compositions for the prevention or treatment of neoplasia comprising a Cox-2 inhibitor in combination with an epidermal growth factor receptor antagonist |
| BR0109165A (pt) * | 2000-03-13 | 2003-04-22 | American Cyanamid Co | Método de tratamento de pólipos colÈnicos |
| US6384051B1 (en) | 2000-03-13 | 2002-05-07 | American Cyanamid Company | Method of treating or inhibiting colonic polyps |
| EP1412367A4 (en) | 2001-06-21 | 2006-05-03 | Ariad Pharma Inc | NEW CHINOLINE AND ITS USE |
| EP1409481B1 (en) | 2001-07-16 | 2006-10-04 | Astrazeneca AB | Quinoline derivatives and their use as tyrosine kinase inhibitors |
| DE60224299T2 (de) * | 2001-10-25 | 2008-12-11 | Novartis Ag | Kombinationsmedikationen mit einem selektiven cyclooxygenase-2-inhibitor |
| 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 |
| EP1542989B1 (en) | 2002-07-31 | 2007-04-18 | Critical Outcome Technologies, Inc. | Protein tyrosine kinase inhibitors |
| EP1551824B1 (en) | 2002-10-09 | 2007-12-12 | Critical Outcome Technologies, Inc. | Protein tyrosine kinase inhibitors |
| CA2506066A1 (en) * | 2002-11-15 | 2004-06-03 | Genomic Health, Inc. | Gene expression profiling of egfr positive cancer |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| KR101218213B1 (ko) | 2003-07-03 | 2013-01-04 | 시토비아 인크. | 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| TW200529846A (en) | 2004-02-20 | 2005-09-16 | Wyeth Corp | 3-quinolinecarbonitrile protein kinase inhibitors |
| EP2168968B1 (en) | 2004-04-02 | 2017-08-23 | OSI Pharmaceuticals, LLC | 6,6-bicyclic ring substituted heterobicyclic protein kinase inhibitors |
| NZ551027A (en) | 2004-04-08 | 2011-01-28 | Targegen Inc | Benzotriazine inhibitors of kinases |
| EP1746999B1 (en) | 2004-05-06 | 2011-11-16 | Warner-Lambert Company LLC | 4-phenylamino-quinazolin-6-yl-amides |
| EP1758601A1 (en) | 2004-06-03 | 2007-03-07 | F.Hoffmann-La Roche Ag | Treatment with cisplatin and an egfr-inhibitor |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| MY167260A (en) | 2005-11-01 | 2018-08-14 | Targegen Inc | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8575164B2 (en) | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
| 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 |
| US8138191B2 (en) | 2007-01-11 | 2012-03-20 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| 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 |
| WO2009079797A1 (en) | 2007-12-26 | 2009-07-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| 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 |
| ES2396613T3 (es) | 2008-05-19 | 2013-02-22 | OSI Pharmaceuticals, LLC | Imidazopirazinas e imidazotriazinas sustituidas |
| 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 |
| PL387312A1 (pl) | 2009-02-19 | 2010-08-30 | Farma-Projekt Spółka Z Ograniczoną Odpowiedzialnością | Zastosowanie sulindaku i/lub jego metabolitu we wspomagającym leczeniu raka jelita grubego u ludzi |
| US20120064072A1 (en) | 2009-03-18 | 2012-03-15 | Maryland Franklin | Combination Cancer Therapy Comprising Administration of an EGFR Inhibitor and an IGF-1R Inhibitor |
| US8513415B2 (en) | 2009-04-20 | 2013-08-20 | OSI Pharmaceuticals, LLC | Preparation of C-pyrazine-methylamines |
| CA2794952C (en) | 2010-04-01 | 2018-05-15 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
| AU2010363329A1 (en) | 2010-11-07 | 2013-05-09 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| WO2012129145A1 (en) | 2011-03-18 | 2012-09-27 | OSI Pharmaceuticals, LLC | Nscle combination therapy |
| RU2606114C2 (ru) * | 2011-06-01 | 2017-01-10 | Джейнус Байотерапьютикс, Инк. | Новые модуляторы иммунной системы |
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| JP2001521926A (ja) * | 1997-11-04 | 2001-11-13 | ファイザー・プロダクツ・インク | 治療上活性の化合物におけるカテコールのインダゾール生物学的等価物置換 |
| EP1039910A1 (en) * | 1997-11-06 | 2000-10-04 | American Cyanamid Company | Use of quinazoline derivatives as tyrosine kinase inhibitors for treating colonic polyps |
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2000
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- 2000-08-02 MX MXPA02001448A patent/MXPA02001448A/es active IP Right Grant
- 2000-08-02 AT AT00950930T patent/ATE341341T1/de not_active IP Right Cessation
- 2000-08-02 EP EP00950930A patent/EP1202746B1/en not_active Expired - Lifetime
- 2000-08-02 PT PT00950930T patent/PT1202746E/pt unknown
- 2000-08-02 DE DE60031127T patent/DE60031127T2/de not_active Expired - Lifetime
- 2000-08-02 AU AU63959/00A patent/AU783116B2/en not_active Ceased
- 2000-08-02 BR BR0013219-5A patent/BR0013219A/pt not_active IP Right Cessation
- 2000-08-02 JP JP2001516570A patent/JP2003507342A/ja active Pending
- 2000-08-02 CN CNB008117977A patent/CN1229142C/zh not_active Expired - Fee Related
- 2000-08-02 NZ NZ517120A patent/NZ517120A/en unknown
- 2000-08-02 HU HU0203162A patent/HUP0203162A3/hu unknown
- 2000-08-02 DK DK00950930T patent/DK1202746T3/da active
- 2000-08-02 HK HK02104004.4A patent/HK1042244A1/zh unknown
- 2000-08-02 KR KR1020027001817A patent/KR20020018201A/ko not_active Ceased
- 2000-08-02 ES ES00950930T patent/ES2272305T3/es not_active Expired - Lifetime
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2002
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2272305T3 (es) | 2007-05-01 |
| CZ2002474A3 (cs) | 2003-02-12 |
| EA006876B1 (ru) | 2006-04-28 |
| AR029763A1 (es) | 2003-07-16 |
| PT1202746E (pt) | 2007-01-31 |
| NO20020663D0 (no) | 2002-02-11 |
| EP1202746B1 (en) | 2006-10-04 |
| AU6395900A (en) | 2001-03-13 |
| HUP0203162A2 (hu) | 2003-01-28 |
| HK1042244A1 (zh) | 2002-08-09 |
| NO20020663L (no) | 2002-04-09 |
| CA2380904C (en) | 2009-02-10 |
| IL147913A0 (en) | 2002-08-14 |
| EP1202746A1 (en) | 2002-05-08 |
| WO2001012227A1 (en) | 2001-02-22 |
| CA2380904A1 (en) | 2001-02-22 |
| HUP0203162A3 (en) | 2006-07-28 |
| ZA200201156B (en) | 2003-05-12 |
| EA200200246A1 (ru) | 2002-08-29 |
| ATE341341T1 (de) | 2006-10-15 |
| KR20020018201A (ko) | 2002-03-07 |
| DK1202746T3 (da) | 2007-01-02 |
| PL353267A1 (en) | 2003-11-03 |
| CN1229142C (zh) | 2005-11-30 |
| BR0013219A (pt) | 2002-04-23 |
| DE60031127D1 (de) | 2006-11-16 |
| NZ517120A (en) | 2004-10-29 |
| CN1370080A (zh) | 2002-09-18 |
| JP2003507342A (ja) | 2003-02-25 |
| DE60031127T2 (de) | 2007-02-01 |
| MXPA02001448A (es) | 2002-07-02 |
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