BR112016011160B1 - Procedimento de fabricação para obtenção de n-benzil-2- (2-nitro-1h-imidazol-1-ila) acetamida - Google Patents
Procedimento de fabricação para obtenção de n-benzil-2- (2-nitro-1h-imidazol-1-ila) acetamida Download PDFInfo
- Publication number
- BR112016011160B1 BR112016011160B1 BR112016011160-5A BR112016011160A BR112016011160B1 BR 112016011160 B1 BR112016011160 B1 BR 112016011160B1 BR 112016011160 A BR112016011160 A BR 112016011160A BR 112016011160 B1 BR112016011160 B1 BR 112016011160B1
- Authority
- BR
- Brazil
- Prior art keywords
- benzyl
- nitro
- acetamide
- imidazol
- synthesis
- Prior art date
Links
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 23
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 claims abstract description 10
- GUDMTEGDXVJZEE-UHFFFAOYSA-N n-benzyl-2-hydroxyacetamide Chemical compound OCC(=O)NCC1=CC=CC=C1 GUDMTEGDXVJZEE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 5
- 239000007790 solid phase Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- CULUWZNBISUWAS-UHFFFAOYSA-N Benznidazole Chemical compound [O-][N+](=O)C1=NC=CN1CC(=O)NCC1=CC=CC=C1 CULUWZNBISUWAS-UHFFFAOYSA-N 0.000 abstract description 13
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- 239000007787 solid Substances 0.000 abstract description 5
- 241000223109 Trypanosoma cruzi Species 0.000 abstract description 4
- 239000011541 reaction mixture Substances 0.000 abstract description 4
- 230000004913 activation Effects 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract description 2
- 206010001935 American trypanosomiasis Diseases 0.000 abstract 2
- 208000024699 Chagas disease Diseases 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- 241000722251 Rhodnius Species 0.000 abstract 1
- 241001414833 Triatoma Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229960004001 benznidazole Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OWNDTEWCMBFNEN-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=N[C]=CN1 OWNDTEWCMBFNEN-UHFFFAOYSA-N 0.000 description 2
- SVOCLWUDDWXHFW-UHFFFAOYSA-N 2-methylsulfanyl-1h-imidazole Chemical compound CSC1=NC=CN1 SVOCLWUDDWXHFW-UHFFFAOYSA-N 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000000884 anti-protozoa Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SRAXAXHQMCQHSH-UHFFFAOYSA-N n-benzyl-2-chloroacetamide Chemical compound ClCC(=O)NCC1=CC=CC=C1 SRAXAXHQMCQHSH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase 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
- JNQNMIJPEYJTIB-UHFFFAOYSA-N 1,1'-biphenyl;phenylmethanol Chemical compound OCC1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 JNQNMIJPEYJTIB-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 230000003569 amebicidal effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000012658 bimolecular nucleophilic substitution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002684 giardicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 methyl 2-chloroacetate ester Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002963 trichomonacidal effect Effects 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SV2013004584 | 2013-11-19 | ||
| SV2013004584A SV2013004584A (es) | 2013-11-19 | 2013-11-19 | Procedimiento de manufactura para obtención de de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida |
| PCT/SV2014/000001 WO2015076760A1 (es) | 2013-11-19 | 2014-11-19 | Procedimiento de manufactura para obtención de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112016011160A2 BR112016011160A2 (enExample) | 2017-08-08 |
| BR112016011160B1 true BR112016011160B1 (pt) | 2022-07-05 |
Family
ID=53179913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112016011160-5A BR112016011160B1 (pt) | 2013-11-19 | 2014-11-19 | Procedimento de fabricação para obtenção de n-benzil-2- (2-nitro-1h-imidazol-1-ila) acetamida |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9765036B2 (enExample) |
| JP (1) | JP6425734B2 (enExample) |
| BR (1) | BR112016011160B1 (enExample) |
| SV (1) | SV2013004584A (enExample) |
| WO (1) | WO2015076760A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017205622A1 (en) * | 2016-05-25 | 2017-11-30 | Savant Neglected Diseases, Llc | Method of making benznidazole |
| WO2019240671A1 (es) * | 2018-06-11 | 2019-12-19 | Ministerio De Educación, Ciencia Y Tecnología | Método de manufactura para la producción de benznidazol y su escalado industrial |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505349A (en) * | 1966-04-18 | 1970-04-07 | Hoffmann La Roche | 2-nitro-imidazolyl-1-acetamides |
| CA2404680C (en) * | 2000-05-17 | 2010-11-16 | Erlinda Handal Vega | Synthesis procedure for biphenylimidazolyl-(1)-phenylmethane and related compounds |
-
2013
- 2013-11-19 SV SV2013004584A patent/SV2013004584A/es active IP Right Grant
-
2014
- 2014-11-19 JP JP2016554169A patent/JP6425734B2/ja active Active
- 2014-11-19 US US15/033,238 patent/US9765036B2/en active Active - Reinstated
- 2014-11-19 BR BR112016011160-5A patent/BR112016011160B1/pt active IP Right Grant
- 2014-11-19 WO PCT/SV2014/000001 patent/WO2015076760A1/es not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US9765036B2 (en) | 2017-09-19 |
| JP6425734B2 (ja) | 2018-11-21 |
| BR112016011160A2 (enExample) | 2017-08-08 |
| WO2015076760A1 (es) | 2015-05-28 |
| US20160289197A1 (en) | 2016-10-06 |
| JP2016539185A (ja) | 2016-12-15 |
| SV2013004584A (es) | 2015-09-07 |
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| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |
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| B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] | ||
| B15K | Others concerning applications: alteration of classification |
Free format text: A CLASSIFICACAO ANTERIOR ERA: C07D 233/91 Ipc: C07D 233/91 (2006.01), A61P 33/00 (2006.01), A61P |
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| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 19/11/2014, OBSERVADAS AS CONDICOES LEGAIS |