JP2005507424A5 - - Google Patents
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- Publication number
- JP2005507424A5 JP2005507424A5 JP2003540178A JP2003540178A JP2005507424A5 JP 2005507424 A5 JP2005507424 A5 JP 2005507424A5 JP 2003540178 A JP2003540178 A JP 2003540178A JP 2003540178 A JP2003540178 A JP 2003540178A JP 2005507424 A5 JP2005507424 A5 JP 2005507424A5
- Authority
- JP
- Japan
- Prior art keywords
- carbamoyl
- lower alkyl
- formula
- cancer
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 cyano, amino Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000003282 alkyl amino group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 7
- 206010038389 Renal cancer Diseases 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 201000010982 kidney cancer Diseases 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 206010005003 Bladder cancer Diseases 0.000 claims 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 4
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims 4
- 206010025537 Malignant anorectal neoplasms Diseases 0.000 claims 4
- 206010027406 Mesothelioma Diseases 0.000 claims 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 210000001072 colon Anatomy 0.000 claims 4
- 206010017758 gastric cancer Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000025402 neoplasm of esophagus Diseases 0.000 claims 4
- 201000010106 skin squamous cell carcinoma Diseases 0.000 claims 4
- 208000014680 small intestine neoplasm Diseases 0.000 claims 4
- 201000011549 stomach cancer Diseases 0.000 claims 4
- 201000005112 urinary bladder cancer Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000006510 metastatic growth Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 208000037062 Polyps Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical class 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MJQZGYWXOBLRPT-CQSZACIVSA-N 6-[4-(chloromethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CCl)C=C1 MJQZGYWXOBLRPT-CQSZACIVSA-N 0.000 description 2
- 241000208199 Buxus sempervirens Species 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- JFFNMSINEFWPKX-CQSZACIVSA-N [4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanol Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CO)C=C1 JFFNMSINEFWPKX-CQSZACIVSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- GEMVUPXNEGKGQL-OAHLLOKOSA-N ethyl 4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 GEMVUPXNEGKGQL-OAHLLOKOSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34092301P | 2001-10-29 | 2001-10-29 | |
| US36165502P | 2002-03-05 | 2002-03-05 | |
| US37936502P | 2002-05-09 | 2002-05-09 | |
| PCT/EP2002/012024 WO2003037897A2 (en) | 2001-10-29 | 2002-10-28 | Use of 7h-pyrrolo[2,3-d]pyrimidine derivatives in the treatment of solid tumor diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005507424A JP2005507424A (ja) | 2005-03-17 |
| JP2005507424A5 true JP2005507424A5 (enExample) | 2006-01-05 |
Family
ID=27407431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003540178A Ceased JP2005507424A (ja) | 2001-10-29 | 2002-10-28 | 固形腫瘍の処置における７Ｈ−ピロロ［２，３−ｄ］ピリミジン誘導体の使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20050038048A1 (enExample) |
| EP (1) | EP1441736A2 (enExample) |
| JP (1) | JP2005507424A (enExample) |
| AU (1) | AU2002349013A1 (enExample) |
| WO (1) | WO2003037897A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005039588A2 (en) * | 2003-10-22 | 2005-05-06 | Novartis Ag | Methods for determining the risk of developing liver and lung toxicity |
| PE20051092A1 (es) * | 2004-01-29 | 2006-01-20 | Novartis Ag | Derivados de pirrolo-pirimidina utiles para el tratamiento de enfermedades proliferativas |
| GB0403606D0 (en) | 2004-02-18 | 2004-03-24 | Novartis Ag | Organic compounds |
| US8975248B2 (en) | 2004-12-15 | 2015-03-10 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Combinations of therapeutic agents for treating cancer |
| CN101365446B (zh) | 2005-07-29 | 2013-05-22 | 雷斯弗洛吉克斯公司 | 预防和治疗复杂疾病的药物组合物及其经由可植入医药装置的递送 |
| RU2008134314A (ru) * | 2006-01-23 | 2010-02-27 | Новартис АГ (CH) | Твердые формы производного пирролопиримидина и их применение в качестве противоопухолевых агентов |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0836605T3 (da) * | 1995-07-06 | 2002-05-13 | Novartis Ag | Pyrrolopyrimidiner og fremgangsmåder til deres fremstilling |
| JP4275733B2 (ja) * | 1996-01-23 | 2009-06-10 | ノバルティス アクチエンゲゼルシャフト | ピロロピリミジンおよびその製造法 |
| GB9925958D0 (en) * | 1999-11-02 | 1999-12-29 | Bundred Nigel J | Therapeutic use |
| CA2427622A1 (en) * | 2000-11-03 | 2002-05-16 | Isaiah J. Fidler | Methods for detecting the efficacy of anticancer treatments |
| EP1339458B1 (en) * | 2000-11-22 | 2007-08-15 | Novartis AG | Combination comprising an agent decreasing vegf activity and an agent decreasing egf activity |
| DE60232719D1 (de) * | 2001-02-27 | 2009-08-06 | Novartis Ag | Kombination enthaltend einen inhibitor der signaltransduktion und ein epothilonderivat |
-
2002
- 2002-10-28 US US10/493,787 patent/US20050038048A1/en not_active Abandoned
- 2002-10-28 EP EP02781294A patent/EP1441736A2/en not_active Withdrawn
- 2002-10-28 JP JP2003540178A patent/JP2005507424A/ja not_active Ceased
- 2002-10-28 AU AU2002349013A patent/AU2002349013A1/en not_active Abandoned
- 2002-10-28 WO PCT/EP2002/012024 patent/WO2003037897A2/en not_active Ceased
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