JP2010522147A5 - - Google Patents
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- Publication number
- JP2010522147A5 JP2010522147A5 JP2009554065A JP2009554065A JP2010522147A5 JP 2010522147 A5 JP2010522147 A5 JP 2010522147A5 JP 2009554065 A JP2009554065 A JP 2009554065A JP 2009554065 A JP2009554065 A JP 2009554065A JP 2010522147 A5 JP2010522147 A5 JP 2010522147A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- methylene
- hydroxyquinoline
- integer
- substituted
- 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.)
- Granted
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
- UZLVOUQDHARTLZ-UHFFFAOYSA-N 5-methylidene-6h-quinolin-8-ol Chemical group C1=CN=C2C(O)=CCC(=C)C2=C1 UZLVOUQDHARTLZ-UHFFFAOYSA-N 0.000 claims description 68
- -1 Boc group Chemical group 0.000 claims description 58
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 40
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- KUFDRRWNPNXBRF-UHFFFAOYSA-N 1,4,8,12-tetrazacyclopentadecane Chemical class C1CNCCCNCCNCCCNC1 KUFDRRWNPNXBRF-UHFFFAOYSA-N 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- TYKPOYYBBXXZCE-UHFFFAOYSA-N 2-methylidene-1h-quinolin-8-ol Chemical group C1=CC(=C)NC2=C1C=CC=C2O TYKPOYYBBXXZCE-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- MNYNYYDIQMZGNK-UHFFFAOYSA-N 5-(naphthalen-1-ylmethylamino)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1NCC1=CC=CC2=CC=CC=C12 MNYNYYDIQMZGNK-UHFFFAOYSA-N 0.000 claims description 3
- IKFSFDAHWNPUFJ-UHFFFAOYSA-N 5-[(8-hydroxyquinolin-5-yl)-(naphthalen-1-ylmethyl)amino]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1N(C=1C2=CC=CN=C2C(O)=CC=1)CC1=CC=CC2=CC=CC=C12 IKFSFDAHWNPUFJ-UHFFFAOYSA-N 0.000 claims description 3
- DOMZDICZCBHSNT-UHFFFAOYSA-N 5-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CN1CCCNCCNCCCNCC1 DOMZDICZCBHSNT-UHFFFAOYSA-N 0.000 claims description 2
- QQAISVITWCCCIC-UHFFFAOYSA-N 5-(1,4,8,12-tetrazacyclopentadec-8-ylmethyl)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CN1CCCNCCCNCCNCCC1 QQAISVITWCCCIC-UHFFFAOYSA-N 0.000 claims description 2
- CKFSZNNHRZDPJV-UHFFFAOYSA-N 5-[(benzylazaniumyl)methyl]quinolin-8-olate Chemical compound C12=CC=CN=C2C(O)=CC=C1CNCC1=CC=CC=C1 CKFSZNNHRZDPJV-UHFFFAOYSA-N 0.000 claims description 2
- NBMGFSVUCFXOOP-UHFFFAOYSA-N 5-[[(4-methylphenyl)methylamino]methyl]quinolin-8-ol Chemical compound C1=CC(C)=CC=C1CNCC1=CC=C(O)C2=NC=CC=C12 NBMGFSVUCFXOOP-UHFFFAOYSA-N 0.000 claims description 2
- LQRGIKZXNZEGIX-UHFFFAOYSA-N 5-[[(8-hydroxyquinolin-5-yl)-[(4-methylphenyl)methyl]amino]methyl]quinolin-8-ol Chemical compound C1=CC(C)=CC=C1CN(C=1C2=CC=CN=C2C(O)=CC=1)CC1=CC=C(O)C2=NC=CC=C12 LQRGIKZXNZEGIX-UHFFFAOYSA-N 0.000 claims description 2
- LOQUUTPFPMJDLD-UHFFFAOYSA-N 5-[[(8-hydroxyquinolin-5-yl)-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CN(C=1C2=CC=CN=C2C(O)=CC=1)CC1=CC=C(C(F)(F)F)C=C1 LOQUUTPFPMJDLD-UHFFFAOYSA-N 0.000 claims description 2
- YOPMGSIGGFDHPL-UHFFFAOYSA-N 5-[[11-[(8-hydroxyquinolin-5-yl)methyl]-1,4,8,11-tetrazacyclotetradec-1-yl]methyl]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CN(CCNCCCNCC1)CCCN1CC1=CC=C(O)C2=NC=CC=C12 YOPMGSIGGFDHPL-UHFFFAOYSA-N 0.000 claims description 2
- HUMSZQCAIUEDCY-UHFFFAOYSA-N 5-[[3-[(8-hydroxyquinolin-5-yl)methylamino]propylamino]methyl]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CNCCCNCC1=CC=C(O)C2=NC=CC=C12 HUMSZQCAIUEDCY-UHFFFAOYSA-N 0.000 claims description 2
- KENDWMBZHXRDQC-UHFFFAOYSA-N 5-[[[4-[[(8-hydroxyquinolin-5-yl)methylamino]methyl]phenyl]methylamino]methyl]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CNCC(C=C1)=CC=C1CNCC1=CC=C(O)C2=NC=CC=C12 KENDWMBZHXRDQC-UHFFFAOYSA-N 0.000 claims description 2
- JDHXHOMUEYWRGQ-UHFFFAOYSA-N ditert-butyl 4,8-bis[(8-hydroxyquinolin-5-yl)methyl]-1,4,8,11-tetrazacyclotetradecane-1,11-dicarboxylate Chemical compound C1CCN(CC=2C3=CC=CN=C3C(O)=CC=2)CCN(C(=O)OC(C)(C)C)CCCN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(O)C2=NC=CC=C12 JDHXHOMUEYWRGQ-UHFFFAOYSA-N 0.000 claims description 2
- DCRHTUSFGYTZTJ-UHFFFAOYSA-N tritert-butyl 11-[(8-hydroxyquinolin-5-yl)methyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN(C(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCCN1CC1=CC=C(O)C2=NC=CC=C12 DCRHTUSFGYTZTJ-UHFFFAOYSA-N 0.000 claims description 2
- MKXQRBASHXALMA-UHFFFAOYSA-N tritert-butyl 12-[(8-hydroxyquinolin-5-yl)methyl]-1,4,8,12-tetrazacyclopentadecane-1,4,8-tricarboxylate Chemical compound C1CCN(C(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCCN(C(=O)OC(C)(C)C)CCCN1CC1=CC=C(O)C2=NC=CC=C12 MKXQRBASHXALMA-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 208000037819 metastatic cancer Diseases 0.000 claims 2
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 2
- 210000004881 tumor cell Anatomy 0.000 claims 2
- KPZWEHRUSPUFCK-UHFFFAOYSA-N 5-(anilinomethyl)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CNC1=CC=CC=C1 KPZWEHRUSPUFCK-UHFFFAOYSA-N 0.000 claims 1
- LWPMUMIMHKHREW-UHFFFAOYSA-N 5-[[benzyl-[(8-hydroxyquinolin-5-yl)methyl]amino]methyl]quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1CN(CC=1C2=CC=CN=C2C(O)=CC=1)CC1=CC=CC=C1 LWPMUMIMHKHREW-UHFFFAOYSA-N 0.000 claims 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims 1
- 208000036832 Adenocarcinoma of ovary Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 1
- 206010061328 Ovarian epithelial cancer Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 201000002313 intestinal cancer Diseases 0.000 claims 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000017830 lymphoblastoma Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000005012 migration Effects 0.000 claims 1
- 238000013508 migration Methods 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 208000013371 ovarian adenocarcinoma Diseases 0.000 claims 1
- 201000006588 ovary adenocarcinoma Diseases 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
- 0 *C(*)c1c(*)c(*)c(*)c(*)c1* Chemical compound *C(*)c1c(*)c(*)c(*)c(*)c1* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR07/02154 | 2007-03-23 | ||
| FR0702154A FR2913976B1 (fr) | 2007-03-23 | 2007-03-23 | Derives de la classe des hydroxyquinoleines aminees pour le traitement de cancers. |
| PCT/FR2008/000399 WO2008135671A2 (fr) | 2007-03-23 | 2008-03-25 | Dérivés de la classe des hydroxyquinoléines aminées pour le traitement de cancers. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010522147A JP2010522147A (ja) | 2010-07-01 |
| JP2010522147A5 true JP2010522147A5 (https=) | 2013-12-12 |
| JP5555494B2 JP5555494B2 (ja) | 2014-07-23 |
Family
ID=38686734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009554065A Expired - Fee Related JP5555494B2 (ja) | 2007-03-23 | 2008-03-25 | 癌を治療するためのアミノ化ヒドロキシキノリン類誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8324243B2 (https=) |
| EP (1) | EP2139860A2 (https=) |
| JP (1) | JP5555494B2 (https=) |
| CN (1) | CN101641332B (https=) |
| AU (1) | AU2008248475B2 (https=) |
| CA (1) | CA2680803A1 (https=) |
| FR (1) | FR2913976B1 (https=) |
| WO (1) | WO2008135671A2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2913976B1 (fr) * | 2007-03-23 | 2013-04-26 | Biopharmed | Derives de la classe des hydroxyquinoleines aminees pour le traitement de cancers. |
| EP2149567A1 (en) * | 2008-07-18 | 2010-02-03 | Bayer Schering Pharma Aktiengesellschaft | Cyclic polyamines for binding phosphatidylserine |
| FR2940289B1 (fr) * | 2008-12-23 | 2014-09-12 | Biopharmed | Derives de la classe des hydroxyquinoleines aminees pour le traitement du cancer du pancreas |
| KR101514285B1 (ko) | 2013-08-09 | 2015-04-22 | 숙명여자대학교산학협력단 | 아미노다이하이드로퀴놀린 화합물 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 함유하는 암 질환의 예방 또는 치료용 약학적 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5736192A (en) * | 1980-08-13 | 1982-02-26 | Nippon Oil Co Ltd | Metal inactivator and its composition |
| IL130324A0 (en) * | 1999-06-07 | 2000-06-01 | Yeda Res & Dev | Pharmaceutical compositions comprising iron chelators for the treatment of neurodegenerative disorders and some novel iron chelators |
| US8058442B2 (en) * | 2002-11-07 | 2011-11-15 | Technion Research And Development Foundation Ltd. | Neuroprotective iron chelators and pharmaceutical compositions comprising them |
| CN1295218C (zh) * | 2004-06-18 | 2007-01-17 | 中国科学院广州化学研究所 | 单官能团8－羟基喹啉金属配合物的烯类单体及其制法和用途 |
| FR2913976B1 (fr) * | 2007-03-23 | 2013-04-26 | Biopharmed | Derives de la classe des hydroxyquinoleines aminees pour le traitement de cancers. |
-
2007
- 2007-03-23 FR FR0702154A patent/FR2913976B1/fr not_active Expired - Fee Related
-
2008
- 2008-03-25 US US12/532,695 patent/US8324243B2/en not_active Expired - Fee Related
- 2008-03-25 CA CA002680803A patent/CA2680803A1/en not_active Abandoned
- 2008-03-25 JP JP2009554065A patent/JP5555494B2/ja not_active Expired - Fee Related
- 2008-03-25 AU AU2008248475A patent/AU2008248475B2/en not_active Ceased
- 2008-03-25 CN CN200880007473.7A patent/CN101641332B/zh not_active Expired - Fee Related
- 2008-03-25 EP EP08787845A patent/EP2139860A2/fr not_active Withdrawn
- 2008-03-25 WO PCT/FR2008/000399 patent/WO2008135671A2/fr not_active Ceased
-
2012
- 2012-11-30 US US13/690,137 patent/US8614230B2/en not_active Expired - Fee Related
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