JP2013542228A5 - - Google Patents
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- JP2013542228A5 JP2013542228A5 JP2013537156A JP2013537156A JP2013542228A5 JP 2013542228 A5 JP2013542228 A5 JP 2013542228A5 JP 2013537156 A JP2013537156 A JP 2013537156A JP 2013537156 A JP2013537156 A JP 2013537156A JP 2013542228 A5 JP2013542228 A5 JP 2013542228A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- egfr
- substituted
- compound
- alkyl
- 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.)
- Pending
Links
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 29
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 29
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 29
- -1 chloro, dimethylamino Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229960002087 pertuzumab Drugs 0.000 claims description 11
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims description 9
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 8
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 8
- 239000002136 L01XE07 - Lapatinib Substances 0.000 claims description 8
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 8
- 229960001433 erlotinib Drugs 0.000 claims description 8
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical group C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 8
- 229960002584 gefitinib Drugs 0.000 claims description 8
- 229960004891 lapatinib Drugs 0.000 claims description 8
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 claims description 8
- 229960000575 trastuzumab Drugs 0.000 claims description 8
- 229960005395 cetuximab Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- CSGQVNMSRKWUSH-IAGOWNOFSA-N (3r,4r)-4-amino-1-[[4-(3-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol Chemical compound COC1=CC=CC(NC=2C3=C(CN4C[C@@H](O)[C@H](N)CC4)C=CN3N=CN=2)=C1 CSGQVNMSRKWUSH-IAGOWNOFSA-N 0.000 claims description 6
- UWXSAYUXVSFDBQ-CYBMUJFWSA-N 4-n-[3-chloro-4-(1,3-thiazol-2-ylmethoxy)phenyl]-6-n-[(4r)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]quinazoline-4,6-diamine Chemical compound C[C@@H]1COC(NC=2C=C3C(NC=4C=C(Cl)C(OCC=5SC=CN=5)=CC=4)=NC=NC3=CC=2)=N1 UWXSAYUXVSFDBQ-CYBMUJFWSA-N 0.000 claims description 6
- QULDDKSCVCJTPV-UHFFFAOYSA-N BIIB021 Chemical compound COC1=C(C)C=NC(CN2C3=NC(N)=NC(Cl)=C3N=C2)=C1C QULDDKSCVCJTPV-UHFFFAOYSA-N 0.000 claims description 6
- 101150029707 ERBB2 gene Proteins 0.000 claims description 6
- 239000002118 L01XE12 - Vandetanib Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000001419 dependent effect Effects 0.000 claims description 6
- 229950010203 nimotuzumab Drugs 0.000 claims description 6
- 229960005560 rindopepimut Drugs 0.000 claims description 6
- 229960005486 vaccine Drugs 0.000 claims description 6
- 229960000241 vandetanib Drugs 0.000 claims description 6
- 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 6
- SWDZPNJZKUGIIH-QQTULTPQSA-N (5z)-n-ethyl-5-(4-hydroxy-6-oxo-3-propan-2-ylcyclohexa-2,4-dien-1-ylidene)-4-[4-(morpholin-4-ylmethyl)phenyl]-2h-1,2-oxazole-3-carboxamide Chemical compound O1NC(C(=O)NCC)=C(C=2C=CC(CN3CCOCC3)=CC=2)\C1=C1/C=C(C(C)C)C(O)=CC1=O SWDZPNJZKUGIIH-QQTULTPQSA-N 0.000 claims description 5
- 206010005003 Bladder cancer Diseases 0.000 claims description 5
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims description 5
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
- 201000010881 cervical cancer Diseases 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 201000004101 esophageal cancer Diseases 0.000 claims description 5
- 206010017758 gastric cancer Diseases 0.000 claims description 5
- 208000005017 glioblastoma Diseases 0.000 claims description 5
- 201000010536 head and neck cancer Diseases 0.000 claims description 5
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
- 229950005069 luminespib Drugs 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 229960001972 panitumumab Drugs 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- 229950007866 tanespimycin Drugs 0.000 claims description 5
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 5
- OAWXZFGKDDFTGS-BYPYZUCNSA-N (2s)-pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(O)=O OAWXZFGKDDFTGS-BYPYZUCNSA-N 0.000 claims description 4
- 101100402572 Arabidopsis thaliana MS5 gene Proteins 0.000 claims description 4
- KUFRQPKVAWMTJO-LMZWQJSESA-N alvespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCCN(C)C)C(=O)C=C1C2=O KUFRQPKVAWMTJO-LMZWQJSESA-N 0.000 claims description 4
- 229950007861 alvespimycin Drugs 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- OIRUWDYJGMHDHJ-AFXVCOSJSA-N retaspimycin hydrochloride Chemical compound Cl.N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(O)C1=CC(O)=C2NCC=C OIRUWDYJGMHDHJ-AFXVCOSJSA-N 0.000 claims description 4
- AVDSOVJPJZVBTC-UHFFFAOYSA-N [4-[2-carbamoyl-5-[6,6-dimethyl-4-oxo-3-(trifluoromethyl)-5,7-dihydroindazol-1-yl]anilino]cyclohexyl] 2-aminoacetate Chemical compound O=C1CC(C)(C)CC2=C1C(C(F)(F)F)=NN2C(C=1)=CC=C(C(N)=O)C=1NC1CCC(OC(=O)CN)CC1 AVDSOVJPJZVBTC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229950008001 matuzumab Drugs 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000035772 mutation Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41111710P | 2010-11-08 | 2010-11-08 | |
| US61/411,117 | 2010-11-08 | ||
| PCT/EP2011/069522 WO2012062694A1 (en) | 2010-11-08 | 2011-11-07 | Use of 2-carboxamide cycloamino urea derivatives in the treatment of egfr dependent diseases or diseases that have acquired resistance to agents that target egfr family members |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016134705A Division JP2016222686A (ja) | 2010-11-08 | 2016-07-07 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013542228A JP2013542228A (ja) | 2013-11-21 |
| JP2013542228A5 true JP2013542228A5 (https=) | 2014-12-25 |
Family
ID=44947083
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013537156A Pending JP2013542228A (ja) | 2010-11-08 | 2011-11-07 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
| JP2016134705A Withdrawn JP2016222686A (ja) | 2010-11-08 | 2016-07-07 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
| JP2018199647A Withdrawn JP2019048822A (ja) | 2010-11-08 | 2018-10-24 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
| JP2020056250A Pending JP2020114849A (ja) | 2010-11-08 | 2020-03-26 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016134705A Withdrawn JP2016222686A (ja) | 2010-11-08 | 2016-07-07 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
| JP2018199647A Withdrawn JP2019048822A (ja) | 2010-11-08 | 2018-10-24 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
| JP2020056250A Pending JP2020114849A (ja) | 2010-11-08 | 2020-03-26 | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して獲得耐性を有する疾患の治療における２−カルボキサミドシクロアミノウレア誘導体の使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US20130209461A1 (https=) |
| EP (1) | EP2637661B1 (https=) |
| JP (4) | JP2013542228A (https=) |
| KR (1) | KR101854484B1 (https=) |
| CN (2) | CN103200943A (https=) |
| AU (1) | AU2011328227B2 (https=) |
| BR (1) | BR112013009624A2 (https=) |
| CA (1) | CA2815492C (https=) |
| MX (1) | MX360157B (https=) |
| RU (1) | RU2589695C2 (https=) |
| TR (1) | TR201802943T4 (https=) |
| WO (1) | WO2012062694A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2014004559A (es) * | 2011-10-14 | 2014-08-01 | Novartis Ag | Derivados de 2-carboxamida cicloamino urea en combinacion con inhibidores de hsp90 para el tratamiento de enfermedades proliferativas. |
| CA2853582A1 (en) * | 2011-11-02 | 2013-05-10 | Novartis Ag | 2-carboxamide cycloamino urea derivatives for use in treating vegf - dependent diseases |
| TR201904980T4 (tr) * | 2012-08-07 | 2019-05-21 | Novartis Ag | Bir B-Raf inhibitörü, bir EGFR inhibitörü ve isteğe bağlı olarak bir PI3K-alfa inhibitörü içeren farmasötik kombinasyonlar. |
| HK1211476A1 (en) * | 2012-08-16 | 2016-05-27 | Novartis Ag | Combination of pi3k inhibitor and c-met inhibitor |
| BR112015025101A2 (pt) * | 2013-04-05 | 2017-07-18 | Sanofi Sa | composição antitumoral que compreende um inibidor pi3kbeta-seletivo e um inibidor pi3kalfa-seletivo |
| SI3076969T1 (sl) * | 2013-12-06 | 2021-12-31 | Novartis Ag | Režim omderjanja izooblike alfa selektivnega zaviralca fosfatidilino- zitol 3-kinaze |
| MY204234A (en) | 2018-08-27 | 2024-08-16 | Regeneron Pharma | Use of raman spectroscopy in downstream purification |
| CA3112043A1 (en) | 2018-09-10 | 2020-03-19 | Mirati Therapeutics, Inc. | Combination therapies |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY130778A (en) * | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| TW200519106A (en) * | 2003-05-02 | 2005-06-16 | Novartis Ag | Organic compounds |
| EP2240475B1 (en) * | 2007-12-20 | 2013-09-25 | Novartis AG | Thiazole derivatives used as pi 3 kinase inhibitors |
| NZ602675A (en) * | 2008-03-18 | 2014-03-28 | Genentech Inc | Combinations of an anti-her2 antibody-drug conjugate and chemotherapeutic agents, and methods of use |
| UA104147C2 (uk) | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
-
2011
- 2011-11-07 CA CA2815492A patent/CA2815492C/en active Active
- 2011-11-07 JP JP2013537156A patent/JP2013542228A/ja active Pending
- 2011-11-07 CN CN2011800538729A patent/CN103200943A/zh active Pending
- 2011-11-07 RU RU2013126485/15A patent/RU2589695C2/ru active
- 2011-11-07 AU AU2011328227A patent/AU2011328227B2/en active Active
- 2011-11-07 EP EP11782111.6A patent/EP2637661B1/en active Active
- 2011-11-07 WO PCT/EP2011/069522 patent/WO2012062694A1/en not_active Ceased
- 2011-11-07 TR TR2018/02943T patent/TR201802943T4/tr unknown
- 2011-11-07 MX MX2013005182A patent/MX360157B/es active IP Right Grant
- 2011-11-07 BR BR112013009624A patent/BR112013009624A2/pt not_active IP Right Cessation
- 2011-11-07 KR KR1020137011803A patent/KR101854484B1/ko active Active
- 2011-11-07 CN CN201510770643.9A patent/CN105412105A/zh active Pending
- 2011-11-07 US US13/879,644 patent/US20130209461A1/en not_active Abandoned
-
2015
- 2015-05-26 US US14/721,064 patent/US20150250778A1/en not_active Abandoned
-
2016
- 2016-07-07 JP JP2016134705A patent/JP2016222686A/ja not_active Withdrawn
-
2018
- 2018-07-12 US US16/033,764 patent/US20180325883A1/en not_active Abandoned
- 2018-10-24 JP JP2018199647A patent/JP2019048822A/ja not_active Withdrawn
-
2019
- 2019-09-17 US US16/573,909 patent/US20200022967A1/en not_active Abandoned
-
2020
- 2020-03-26 JP JP2020056250A patent/JP2020114849A/ja active Pending
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