JP2019517500A5 - - Google Patents
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- Publication number
- JP2019517500A5 JP2019517500A5 JP2018562928A JP2018562928A JP2019517500A5 JP 2019517500 A5 JP2019517500 A5 JP 2019517500A5 JP 2018562928 A JP2018562928 A JP 2018562928A JP 2018562928 A JP2018562928 A JP 2018562928A JP 2019517500 A5 JP2019517500 A5 JP 2019517500A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexyl
- diamine
- purine
- aminomethyl
- aminopurine compound
- 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
- -1 aminopurine compound Chemical class 0.000 claims description 136
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 122
- 238000000034 method Methods 0.000 claims description 42
- 239000013543 active substance Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 201000002311 trypanosomiasis Diseases 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 12
- 208000029080 human African trypanosomiasis Diseases 0.000 claims description 12
- 208000004554 Leishmaniasis Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- ARFHIAQFJWUCFH-IZZDOVSWSA-N Nifurtimox Chemical compound CC1CS(=O)(=O)CCN1\N=C\C1=CC=C([N+]([O-])=O)O1 ARFHIAQFJWUCFH-IZZDOVSWSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229960002644 nifurtimox Drugs 0.000 claims description 8
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical group C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims description 8
- 229960004448 pentamidine Drugs 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 208000024699 Chagas disease Diseases 0.000 claims description 6
- 241000223109 Trypanosoma cruzi Species 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 4
- KMJWBVJQFGRCEB-UHFFFAOYSA-O 4-n-(4-imino-1,2-dimethylquinolin-6-yl)-1,6-dimethylpyrimidin-1-ium-2,4-diamine Chemical compound C=1C=C2N(C)C(C)=CC(=N)C2=CC=1NC1=CC(C)=[N+](C)C(N)=N1 KMJWBVJQFGRCEB-UHFFFAOYSA-O 0.000 claims description 4
- CULUWZNBISUWAS-UHFFFAOYSA-N Benznidazole Chemical group [O-][N+](=O)C1=NC=CN1CC(=O)NCC1=CC=CC=C1 CULUWZNBISUWAS-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- JCYZMTMYPZHVBF-UHFFFAOYSA-N Melarsoprol Chemical compound NC1=NC(N)=NC(NC=2C=CC(=CC=2)[As]2SC(CO)CS2)=N1 JCYZMTMYPZHVBF-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 241000159552 Trypanosoma avium Species 0.000 claims description 4
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 4
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical group [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229960004001 benznidazole Drugs 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- XNYZHCFCZNMTFY-UHFFFAOYSA-N diminazene Chemical compound C1=CC(C(=N)N)=CC=C1N\N=N\C1=CC=C(C(N)=N)C=C1 XNYZHCFCZNMTFY-UHFFFAOYSA-N 0.000 claims description 4
- 229950007095 diminazene Drugs 0.000 claims description 4
- VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 claims description 4
- 229960002759 eflornithine Drugs 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- CFUQBFQTFMOZBK-QUCCMNQESA-N ibazocine Chemical compound C12=CC(O)=CC=C2C[C@H]2N(CC=C(C)C)CC[C@]1(C)C2(C)C CFUQBFQTFMOZBK-QUCCMNQESA-N 0.000 claims description 4
- 229960004125 ketoconazole Drugs 0.000 claims description 4
- MGEOLZFMLHYCFZ-UHFFFAOYSA-N melarsomine Chemical compound C1=CC([As](SCCN)SCCN)=CC=C1NC1=NC(N)=NC(N)=N1 MGEOLZFMLHYCFZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960002234 melarsomine Drugs 0.000 claims description 4
- 229960001728 melarsoprol Drugs 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 claims description 4
- 229960003775 miltefosine Drugs 0.000 claims description 4
- 229960005065 paromomycin sulfate Drugs 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 4
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims description 4
- 229960005314 suramin Drugs 0.000 claims description 4
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- GYOJVHYUDOQQQS-UHFFFAOYSA-N 4-[2-(tert-butylamino)-8-(2,4,6-trifluoroanilino)purin-9-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1N1C2=NC(NC(C)(C)C)=NC=C2N=C1NC1=C(F)C=C(F)C=C1F GYOJVHYUDOQQQS-UHFFFAOYSA-N 0.000 claims description 2
- VYVOHVKGNLXHLJ-UHFFFAOYSA-N 4-[2-(tert-butylamino)-8-(2,4-difluoroanilino)purin-9-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1N1C2=NC(NC(C)(C)C)=NC=C2N=C1NC1=CC=C(F)C=C1F VYVOHVKGNLXHLJ-UHFFFAOYSA-N 0.000 claims description 2
- ZOAZCBMVZIQJQI-UHFFFAOYSA-N 4-[2-(tert-butylamino)-8-(2,6-difluoroanilino)purin-9-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1N1C2=NC(NC(C)(C)C)=NC=C2N=C1NC1=C(F)C=CC=C1F ZOAZCBMVZIQJQI-UHFFFAOYSA-N 0.000 claims description 2
- IFUOOSWRXRCWHC-UHFFFAOYSA-N 9-(3-aminocyclobutyl)-2-N-tert-butyl-8-N-(3,4-dichlorophenyl)purine-2,8-diamine Chemical compound NC1CC(C1)N1C2=NC(=NC=C2N=C1NC1=CC(=C(C=C1)Cl)Cl)NC(C)(C)C IFUOOSWRXRCWHC-UHFFFAOYSA-N 0.000 claims description 2
- ZVHBMRXTHZFMLD-UHFFFAOYSA-N 9-(3-aminocyclobutyl)-8-N-(3-chlorophenyl)-2-N-(4-methyloxan-4-yl)purine-2,8-diamine Chemical compound NC1CC(C1)N1C2=NC(=NC=C2N=C1NC1=CC(=CC=C1)Cl)NC1(CCOCC1)C ZVHBMRXTHZFMLD-UHFFFAOYSA-N 0.000 claims description 2
- UXIRDFCRTXCHEQ-UHFFFAOYSA-N 9-(4-aminocyclohexyl)-8-N-[2-fluoro-5-(trifluoromethyl)phenyl]-2-N-(4-methyloxan-4-yl)purine-2,8-diamine Chemical compound NC1CCC(CC1)N1C2=NC(=NC=C2N=C1NC1=C(C=CC(=C1)C(F)(F)F)F)NC1(CCOCC1)C UXIRDFCRTXCHEQ-UHFFFAOYSA-N 0.000 claims description 2
- QSCFWQFZJLPUFU-QFBILLFUSA-N 9-[(1R,3S)-3-(aminomethyl)cyclohexyl]-8-N-(3-chlorophenyl)-2-N-(4-methyloxan-4-yl)purine-2,8-diamine Chemical compound NC[C@@H]1C[C@@H](CCC1)N1C2=NC(=NC=C2N=C1NC1=CC(=CC=C1)Cl)NC1(CCOCC1)C QSCFWQFZJLPUFU-QFBILLFUSA-N 0.000 claims description 2
- UNDJICXVHIWORE-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-N-(3-chlorophenyl)-2-N-(4-methyloxan-4-yl)purine-2,8-diamine Chemical compound NCC1=CC=C(C=C1)N1C2=NC(=NC=C2N=C1NC1=CC(=CC=C1)Cl)NC1(CCOCC1)C UNDJICXVHIWORE-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 2
- UGKOYGZYLRKTJH-UHFFFAOYSA-O 3-[2-(3-amino-5-ethyl-6-phenylphenanthridin-5-ium-8-yl)iminohydrazinyl]benzenecarboximidamide Chemical compound C12=CC(N=NNC=3C=C(C=CC=3)C(N)=N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 UGKOYGZYLRKTJH-UHFFFAOYSA-O 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662344759P | 2016-06-02 | 2016-06-02 | |
| US62/344,759 | 2016-06-02 | ||
| PCT/US2017/035413 WO2017210408A1 (en) | 2016-06-02 | 2017-06-01 | Animal and human anti-trypanosomonal and anti-leishmania agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019517500A JP2019517500A (ja) | 2019-06-24 |
| JP2019517500A5 true JP2019517500A5 (https=) | 2020-07-02 |
| JP6949057B2 JP6949057B2 (ja) | 2021-10-13 |
Family
ID=60477945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018562928A Active JP6949057B2 (ja) | 2016-06-02 | 2017-06-01 | 動物及びヒトの抗トリパノソーマならびに抗リーシュマニア薬 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US10010555B2 (https=) |
| EP (1) | EP3464312A4 (https=) |
| JP (1) | JP6949057B2 (https=) |
| CN (1) | CN109476696B (https=) |
| AR (1) | AR108665A1 (https=) |
| TW (1) | TW201802093A (https=) |
| WO (1) | WO2017210408A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6970126B2 (ja) * | 2016-06-02 | 2021-11-24 | セルジーン コーポレイション | 動物及びヒトの抗マラリア薬 |
| TW202202498A (zh) * | 2020-07-01 | 2022-01-16 | 大陸商四川海思科製藥有限公司 | 一種並環雜環衍生物及其在醫藥上的應用 |
| CN120441543B (zh) * | 2025-07-08 | 2025-10-03 | 安徽红杉生物医药科技有限公司 | 一种喹匹拉明及其中间体的制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4914086A (en) * | 1987-12-18 | 1990-04-03 | University Patents, Inc. | Method for treating African human and veterinary trypanosomiases |
| DK120892D0 (da) * | 1992-09-30 | 1992-09-30 | Statens Seruminstitut | Treatment and prophylaxis of diseases caused by parasites, fungi or bacteria |
| US5773424A (en) * | 1994-12-16 | 1998-06-30 | Research Corporation Technologies, Inc. | Treatment of toxoplasmosis |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| JP2008510766A (ja) * | 2004-08-27 | 2008-04-10 | ゲーペーツェー ビオテック アーゲー | ピリミジン誘導体 |
| US7521446B2 (en) | 2005-01-13 | 2009-04-21 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
| US7759342B2 (en) * | 2005-01-13 | 2010-07-20 | Signal Pharmaceuticals, Llc | Methods of treatment and prevention using haloaryl substituted aminopurines |
| US7723340B2 (en) * | 2005-01-13 | 2010-05-25 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
| GB0610317D0 (en) * | 2006-05-24 | 2006-07-05 | Medical Res Council | Antiparasitic compounds and compositions |
| CA2667345C (en) | 2006-10-27 | 2016-03-22 | Signal Pharmaceuticals, Llc | Solid forms comprising 4-[9-(tetrahydro-furan-3-yl)-8-(2,4,6-trifluoro-phenylamino)-9h-purin-2-ylamino]-cyclohexan-1-ol, compositions thereof, and uses therewith |
| KR20090112732A (ko) | 2007-01-26 | 2009-10-28 | 아이알엠 엘엘씨 | 플라스모듐 관련 질환의 치료를 위한 키나제 억제제로서의 퓨린 화합물 및 조성물 |
| EP2209786B1 (en) * | 2007-10-05 | 2013-02-27 | Verastem, Inc. | Pyrimidine substituted purine derivatives |
| WO2009143865A1 (en) * | 2008-05-30 | 2009-12-03 | Xigen S.A. | Use of cell-permeable peptide inhibitors of the jnk signal transduction pathway for the treatment of various diseases |
| UA103195C2 (uk) * | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| BRPI0917013A2 (pt) * | 2008-08-11 | 2016-02-16 | Glaxosmithkline Llc | métodos para tratar doenças alérgicas e outras condições inflamatórias, e para tratar ou prevenir doença, composto, composição farmacêutica, e, uso de um composto |
| WO2010059418A1 (en) * | 2008-11-19 | 2010-05-27 | The Government Of The U.S.A. As Represented By The Secretary Of The Dept. Of Health & Human Services | Substituted triazine and purine compounds, methods of inhibiting cruzain and rhodesain and methods of treating chagas disease and african trypanosomiasis |
| EP2847201B1 (en) * | 2012-05-07 | 2017-08-16 | The University of Queensland | 6-oxopurine phosphoribosyltransferase inhibitors |
| EP2964648B1 (en) * | 2013-03-05 | 2016-11-16 | Merck Patent GmbH | 9-(aryl or heteroaryl)-2-(pyrazolyl, pyrrolidinyl or cyclopentyl)aminopurine derivatives as anticancer agents |
| WO2014151630A2 (en) * | 2013-03-15 | 2014-09-25 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| US9512124B2 (en) * | 2014-10-06 | 2016-12-06 | Signal Pharmaceuticals, Llc | Substituted aminopurine compounds, compositions thereof, and methods of treatment therewith |
-
2017
- 2017-06-01 EP EP17807469.6A patent/EP3464312A4/en active Pending
- 2017-06-01 US US15/611,061 patent/US10010555B2/en active Active
- 2017-06-01 AR ARP170101506A patent/AR108665A1/es unknown
- 2017-06-01 CN CN201780045066.4A patent/CN109476696B/zh active Active
- 2017-06-01 WO PCT/US2017/035413 patent/WO2017210408A1/en not_active Ceased
- 2017-06-01 TW TW106118079A patent/TW201802093A/zh unknown
- 2017-06-01 JP JP2018562928A patent/JP6949057B2/ja active Active
-
2018
- 2018-06-06 US US16/000,969 patent/US10420772B2/en active Active
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