UY24945A1 - Proceso para preparar haluros de acido o-(3-amino-2-hidroxi- propil)-hidroximico - Google Patents
Proceso para preparar haluros de acido o-(3-amino-2-hidroxi- propil)-hidroximicoInfo
- Publication number
- UY24945A1 UY24945A1 UY24945A UY24945A UY24945A1 UY 24945 A1 UY24945 A1 UY 24945A1 UY 24945 A UY24945 A UY 24945A UY 24945 A UY24945 A UY 24945A UY 24945 A1 UY24945 A1 UY 24945A1
- Authority
- UY
- Uruguay
- Prior art keywords
- formula
- substituted
- hydroxy
- represented
- salt
- Prior art date
Links
- -1 3-AMINO-2-HYDROXY-PROPYL Chemical class 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 150000004820 halides Chemical class 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- 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 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 231100000915 pathological change Toxicity 0.000 abstract 1
- 230000036285 pathological change Effects 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 230000002792 vascular Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Proceso para preparar haluros de Ácido O-(3-amino-2-hidroxi-propil)-hidroximico de fórmula (I), representada en la figura 1, y sus sales de adición ácidas y las formas ópticamente activas de los compuestos, donde: R1 es fenilo, piridilo o tienilo o fenilo sustituido, en el cual uno o más sustituyentes pueden ser halo y/o haloalquilo y/o nitrilo; X es halo; R2 y R3 son, cada uno, un alquilo inferiro ramificado o lineal, o un un heterociclo de 5 a 7 miembros saturados que puede contener un heteroátomo adicional y puede ser sustituido; dicho proceso caracterizado porque comprende la reacción de una oxima de carboxamida de fórmula (II) representada en la figura 2, con una sal de 3-hidroxi-acetidino de fórmula (III), representada en la figura 3, donde Y es un anión que forma una sal en un medio alcohólico inferiro, preferentemente medio etanólico, alcalinizado mediante mediante un hidróxido alcalino; diazotizar la oxioma de carboxamida sustituida en O resultante con nitrito de sodio en presencia de haluro de hidrógeno; descomponer la sal de diazonio, aislar el producto obtenido y, si fuera conveniente, separar los enantiómeros opticamente activos y/o hacer reaccionar la base resultante con ácido mineral u orgánico; y antes de diazotar el producto intermedio de oxima sustituida en O obteniendo, la mezcla de la reacción es neutralizada y el solvente orgánico eliminado. Los compuestos de fórmula (I) son de utilidad en el tratamiento de cambios patológicos en el sistema vascular asociados con la diabetes mellitus, en particular con la angipatía diabética.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9700699A HU220971B1 (hu) | 1997-04-03 | 1997-04-03 | Eljárás 0-(3-amino-2-hidroxi-propil)-hidroximsav-halogenidek előállítására |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UY24945A1 true UY24945A1 (es) | 1998-09-28 |
Family
ID=89994956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY24945A UY24945A1 (es) | 1997-04-03 | 1998-04-02 | Proceso para preparar haluros de acido o-(3-amino-2-hidroxi- propil)-hidroximico |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6180787B1 (es) |
| EP (1) | EP0975585A1 (es) |
| JP (1) | JP2001521498A (es) |
| KR (1) | KR20010005943A (es) |
| CN (1) | CN1251574A (es) |
| AP (1) | AP9901646A0 (es) |
| AR (1) | AR012308A1 (es) |
| AU (1) | AU737994B2 (es) |
| BG (1) | BG63116B1 (es) |
| BR (1) | BR9714717A (es) |
| CA (1) | CA2285360A1 (es) |
| CO (1) | CO4940491A1 (es) |
| EA (1) | EA199900899A1 (es) |
| EE (1) | EE03868B1 (es) |
| EG (1) | EG22104A (es) |
| HR (1) | HRP980175A2 (es) |
| HU (1) | HU220971B1 (es) |
| ID (1) | ID20016A (es) |
| IL (1) | IL132048A0 (es) |
| IS (1) | IS5174A (es) |
| MA (1) | MA26143A1 (es) |
| NO (1) | NO312027B1 (es) |
| NZ (1) | NZ500020A (es) |
| PE (1) | PE83299A1 (es) |
| PL (1) | PL336072A1 (es) |
| SK (1) | SK134899A3 (es) |
| TN (1) | TNSN98046A1 (es) |
| TR (1) | TR199902207T2 (es) |
| TW (1) | TW455573B (es) |
| UY (1) | UY24945A1 (es) |
| WO (1) | WO1998043948A1 (es) |
| YU (1) | YU49499A (es) |
| ZA (1) | ZA982755B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9900475D0 (en) * | 1999-02-26 | 1999-04-28 | Biorex Kutato Fejlesztoe Kft | O-(3-piperidino-2-hydroxy-1-propyl)-hiyroximic acid-halogenid derivative, it's use for treating insulin resistance, and pharmaceutical compositions containing them as active component |
| AU2003202104B8 (en) | 2002-01-11 | 2008-10-02 | Cytrx Corporation | Carboxamidine derivatives and their use in the treatment of vascular diseases |
| HUP0303584A3 (en) | 2003-10-30 | 2009-12-28 | Cytrx Corp | Use of a hydroximic acid halide derivative in the treatment of neurodegenerative diseases |
| CA2859469A1 (en) * | 2011-12-23 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Chemical compounds |
| KR102051174B1 (ko) * | 2012-06-14 | 2019-12-02 | 노파르티스 아게 | 아제티디늄-함유 공중합체 및 그의 용도 |
| CN103804309B (zh) * | 2012-11-09 | 2019-08-02 | 广州喜鹊医药有限公司 | 一种氯肟类化合物及其制备方法和在制药中的应用 |
| US20230416224A1 (en) | 2020-11-19 | 2023-12-28 | Zevra Denmark A/S | Processes for preparing arimoclomol citrate and intermediates thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU207305B (en) * | 1988-03-23 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Improved process for producing amidoxime derivatives |
| HU207988B (en) * | 1988-10-20 | 1993-07-28 | Biorex Kutato Fejlesztoe Kft | Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components |
| HUT54347A (en) * | 1989-01-10 | 1991-02-28 | Chinoin Gyogyszer Es Vegyeszet | Improved process for producing amidoximes |
-
1997
- 1997-04-03 HU HU9700699A patent/HU220971B1/hu not_active IP Right Cessation
- 1997-12-05 KR KR1019997009020A patent/KR20010005943A/ko not_active Application Discontinuation
- 1997-12-05 WO PCT/HU1997/000082 patent/WO1998043948A1/en not_active Application Discontinuation
- 1997-12-05 CN CN97182087A patent/CN1251574A/zh active Pending
- 1997-12-05 EP EP97947819A patent/EP0975585A1/en not_active Withdrawn
- 1997-12-05 AP APAP/P/1999/001646A patent/AP9901646A0/en unknown
- 1997-12-05 BR BR9714717-6A patent/BR9714717A/pt not_active Application Discontinuation
- 1997-12-05 TR TR1999/02207T patent/TR199902207T2/xx unknown
- 1997-12-05 JP JP54132298A patent/JP2001521498A/ja active Pending
- 1997-12-05 AU AU54055/98A patent/AU737994B2/en not_active Ceased
- 1997-12-05 PL PL97336072A patent/PL336072A1/xx unknown
- 1997-12-05 SK SK1348-99A patent/SK134899A3/sk unknown
- 1997-12-05 EA EA199900899A patent/EA199900899A1/ru unknown
- 1997-12-05 EE EEP199900438A patent/EE03868B1/xx not_active IP Right Cessation
- 1997-12-05 NZ NZ500020A patent/NZ500020A/en unknown
- 1997-12-05 CA CA002285360A patent/CA2285360A1/en not_active Abandoned
- 1997-12-05 US US09/402,267 patent/US6180787B1/en not_active Expired - Fee Related
- 1997-12-15 YU YU49499A patent/YU49499A/sh unknown
-
1998
- 1998-03-30 MA MA25016A patent/MA26143A1/fr unknown
- 1998-03-31 EG EG36098A patent/EG22104A/xx active
- 1998-04-01 ZA ZA982755A patent/ZA982755B/xx unknown
- 1998-04-02 AR ARP980101495A patent/AR012308A1/es not_active Application Discontinuation
- 1998-04-02 PE PE1998000247A patent/PE83299A1/es not_active Application Discontinuation
- 1998-04-02 TN TNTNSN98046A patent/TNSN98046A1/fr unknown
- 1998-04-02 UY UY24945A patent/UY24945A1/es not_active IP Right Cessation
- 1998-04-03 CO CO98018891A patent/CO4940491A1/es unknown
- 1998-04-03 ID IDP980507A patent/ID20016A/id unknown
- 1998-04-03 HR HRP9700699A patent/HRP980175A2/hr not_active Application Discontinuation
- 1998-04-07 TW TW087105087A patent/TW455573B/zh not_active IP Right Cessation
-
1999
- 1999-09-10 IS IS5174A patent/IS5174A/is unknown
- 1999-09-23 NO NO19994628A patent/NO312027B1/no not_active IP Right Cessation
- 1999-09-23 IL IL13204899A patent/IL132048A0/xx unknown
- 1999-11-02 BG BG103847A patent/BG63116B1/bg unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| VENC | Patent expired |
Effective date: 20180402 |