ES2696350T3 - Compuestos de triaminopirimidina útiles para evitar o tratar la malaria - Google Patents
Compuestos de triaminopirimidina útiles para evitar o tratar la malaria Download PDFInfo
- Publication number
- ES2696350T3 ES2696350T3 ES15713170T ES15713170T ES2696350T3 ES 2696350 T3 ES2696350 T3 ES 2696350T3 ES 15713170 T ES15713170 T ES 15713170T ES 15713170 T ES15713170 T ES 15713170T ES 2696350 T3 ES2696350 T3 ES 2696350T3
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- Prior art keywords
- methyl
- compound
- cyclopropyl
- diamine
- pyridyl
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- 201000004792 malaria Diseases 0.000 title claims description 38
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical class NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 8
- -1 complexes Chemical class 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 43
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 241000224016 Plasmodium Species 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002207 metabolite Substances 0.000 claims description 11
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- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
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- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- IOTAOYHKWICOBK-UHFFFAOYSA-N 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione;hydrochloride Chemical compound Cl.CC(C)N=C(N)\N=C(/N)NC1=CC=C(Cl)C=C1.O=C1C(=O)C2=CC=CC=C2C(O)=C1C(CC1)CCC1C1=CC=C(Cl)C=C1 IOTAOYHKWICOBK-UHFFFAOYSA-N 0.000 claims description 2
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- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 244000000040 protozoan parasite Species 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
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- 102000005962 receptors Human genes 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- UGOGIUREIICPLT-UHFFFAOYSA-N spiro[1h-indole-3,1'-pyrido[3,4-b]indole]-2-one Chemical compound C12=NC3=CC=CC=C3C1=CC=NC12C2=CC=CC=C2NC1=O UGOGIUREIICPLT-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- DATRVIMZZZVHMP-QMMMGPOBSA-N tert-butyl (2s)-2-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CNCCN1C(=O)OC(C)(C)C DATRVIMZZZVHMP-QMMMGPOBSA-N 0.000 description 1
- WEGGXPBGPKOATN-UHFFFAOYSA-N tert-butyl 4-[2-[(5-chloro-4-cyclopropyl-6-methylpyridin-2-yl)amino]-4-[(2-methyltriazol-4-yl)amino]pyrimidin-5-yl]-2-methylpiperazine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C(CN(CC1)C=1C(=NC(=NC1)NC1=NC(=C(C(=C1)C1CC1)Cl)C)NC1=NN(N=C1)C)C WEGGXPBGPKOATN-UHFFFAOYSA-N 0.000 description 1
- IBHNZYGOIQANKV-UHFFFAOYSA-N tert-butyl 4-[2-chloro-4-[(1-ethyl-5-methylpyrazol-3-yl)amino]pyrimidin-5-yl]-2-methylpiperazine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C(CN(CC1)C=1C(=NC(=NC1)Cl)NC1=NN(C(=C1)C)CC)C IBHNZYGOIQANKV-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2142CH2014 | 2014-04-28 | ||
| PCT/EP2015/056496 WO2015165660A1 (en) | 2014-04-28 | 2015-03-26 | Triaminopyrimidine compounds useful for preventing or treating malaria |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2696350T3 true ES2696350T3 (es) | 2019-01-15 |
Family
ID=52779638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15713170T Active ES2696350T3 (es) | 2014-04-28 | 2015-03-26 | Compuestos de triaminopirimidina útiles para evitar o tratar la malaria |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9957253B2 (https=) |
| EP (1) | EP3137455B1 (https=) |
| JP (1) | JP6529983B2 (https=) |
| CN (1) | CN106255685B (https=) |
| AP (1) | AP2016009570A0 (https=) |
| BR (1) | BR112016024467B1 (https=) |
| CA (1) | CA2946654C (https=) |
| CY (1) | CY1120700T1 (https=) |
| DK (1) | DK3137455T3 (https=) |
| ES (1) | ES2696350T3 (https=) |
| HR (1) | HRP20181816T1 (https=) |
| HU (1) | HUE042043T2 (https=) |
| LT (1) | LT3137455T (https=) |
| MX (1) | MX374458B (https=) |
| MY (1) | MY178971A (https=) |
| PH (1) | PH12016502322B1 (https=) |
| PL (1) | PL3137455T3 (https=) |
| PT (1) | PT3137455T (https=) |
| RS (1) | RS58124B1 (https=) |
| SI (1) | SI3137455T1 (https=) |
| SM (1) | SMT201800588T1 (https=) |
| WO (1) | WO2015165660A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105699584B (zh) * | 2016-02-03 | 2018-02-09 | 昆药集团股份有限公司 | 一种蒿甲醚相关物质的检测方法 |
| WO2018079629A1 (ja) | 2016-10-26 | 2018-05-03 | カルナバイオサイエンス株式会社 | 抗マラリア活性を有する新規ピリミジン誘導体 |
| CN106727584A (zh) * | 2017-02-08 | 2017-05-31 | 于贵庆 | 一种治疗骨病的药物组合物 |
| JP2020532513A (ja) * | 2017-09-05 | 2020-11-12 | カディラ ヘルスケア リミティド | トリアミノピリミジン化合物およびその中間体の調製方法 |
| CN117327007B (zh) * | 2023-09-26 | 2024-09-13 | 上海陶术生物科技有限公司 | 一种vt107的制备方法 |
| WO2025115034A1 (en) * | 2023-11-30 | 2025-06-05 | Zydus Lifesciences Limited | A process for the preparation of a triaminopyrimidine compound and novel intermediates thereof |
| EP4574143A1 (en) | 2023-12-21 | 2025-06-25 | Universität Regensburg | Inhibitors of plasmodia remodeling enzymes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003286711A1 (en) * | 2002-10-25 | 2004-05-13 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| RU2405778C2 (ru) * | 2004-09-30 | 2010-12-10 | Тиботек Фармасьютикалз Лтд. | 5-гетероциклилпиримидины, ингибирующие вич |
| WO2014058685A1 (en) * | 2012-10-08 | 2014-04-17 | Merck Sharp & Dohme Corp. | Inhibitors of irak4 activity |
-
2015
- 2015-03-26 EP EP15713170.7A patent/EP3137455B1/en active Active
- 2015-03-26 DK DK15713170.7T patent/DK3137455T3/en active
- 2015-03-26 HU HUE15713170A patent/HUE042043T2/hu unknown
- 2015-03-26 CN CN201580022719.8A patent/CN106255685B/zh active Active
- 2015-03-26 JP JP2016562579A patent/JP6529983B2/ja active Active
- 2015-03-26 BR BR112016024467-2A patent/BR112016024467B1/pt active IP Right Grant
- 2015-03-26 MX MX2016014166A patent/MX374458B/es active IP Right Grant
- 2015-03-26 AP AP2016009570A patent/AP2016009570A0/en unknown
- 2015-03-26 PT PT15713170T patent/PT3137455T/pt unknown
- 2015-03-26 RS RS20181368A patent/RS58124B1/sr unknown
- 2015-03-26 CA CA2946654A patent/CA2946654C/en active Active
- 2015-03-26 ES ES15713170T patent/ES2696350T3/es active Active
- 2015-03-26 PL PL15713170T patent/PL3137455T3/pl unknown
- 2015-03-26 US US15/307,382 patent/US9957253B2/en active Active
- 2015-03-26 SM SM20180588T patent/SMT201800588T1/it unknown
- 2015-03-26 HR HRP20181816TT patent/HRP20181816T1/hr unknown
- 2015-03-26 SI SI201530475T patent/SI3137455T1/sl unknown
- 2015-03-26 MY MYPI2016703966A patent/MY178971A/en unknown
- 2015-03-26 WO PCT/EP2015/056496 patent/WO2015165660A1/en not_active Ceased
- 2015-03-26 LT LTEP15713170.7T patent/LT3137455T/lt unknown
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2016
- 2016-11-22 PH PH12016502322A patent/PH12016502322B1/en unknown
-
2018
- 2018-09-27 CY CY181100997T patent/CY1120700T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AP2016009570A0 (en) | 2016-11-30 |
| CA2946654A1 (en) | 2015-11-05 |
| MY178971A (en) | 2020-10-26 |
| CN106255685B (zh) | 2019-08-20 |
| EP3137455A1 (en) | 2017-03-08 |
| CN106255685A (zh) | 2016-12-21 |
| US20170050951A1 (en) | 2017-02-23 |
| RS58124B1 (sr) | 2019-02-28 |
| MX374458B (es) | 2025-03-06 |
| JP2017514804A (ja) | 2017-06-08 |
| PH12016502322B1 (en) | 2022-03-23 |
| PL3137455T3 (pl) | 2019-01-31 |
| MX2016014166A (es) | 2017-02-14 |
| PH12016502322A1 (en) | 2017-01-30 |
| BR112016024467B1 (pt) | 2022-11-29 |
| LT3137455T (lt) | 2018-10-25 |
| CA2946654C (en) | 2022-08-23 |
| EP3137455B1 (en) | 2018-08-15 |
| BR112016024467A2 (pt) | 2017-08-15 |
| WO2015165660A1 (en) | 2015-11-05 |
| HK1231478A1 (en) | 2017-12-22 |
| CY1120700T1 (el) | 2019-12-11 |
| SI3137455T1 (sl) | 2019-01-31 |
| US9957253B2 (en) | 2018-05-01 |
| HRP20181816T1 (hr) | 2018-12-28 |
| PT3137455T (pt) | 2018-11-21 |
| DK3137455T3 (en) | 2018-12-10 |
| SMT201800588T1 (it) | 2019-01-11 |
| JP6529983B2 (ja) | 2019-06-12 |
| HUE042043T2 (hu) | 2019-06-28 |
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