HRP20090514T1 - Novi postupak dobivanja kvaternih kiselih i amonijevih soli - Google Patents
Novi postupak dobivanja kvaternih kiselih i amonijevih soli Download PDFInfo
- Publication number
- HRP20090514T1 HRP20090514T1 HR20090514T HRP20090514T HRP20090514T1 HR P20090514 T1 HRP20090514 T1 HR P20090514T1 HR 20090514 T HR20090514 T HR 20090514T HR P20090514 T HRP20090514 T HR P20090514T HR P20090514 T1 HRP20090514 T1 HR P20090514T1
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- 238000000034 method Methods 0.000 title claims abstract 12
- 239000002253 acid Substances 0.000 title 1
- 150000003863 ammonium salts Chemical class 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract 5
- 150000002148 esters Chemical class 0.000 claims abstract 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract 5
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 4
- 239000011707 mineral Substances 0.000 claims 4
- 235000010755 mineral Nutrition 0.000 claims 4
- 239000012429 reaction media Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- -1 2-(4-chlorobenzoylamino)ethyl group Chemical group 0.000 claims 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 235000010216 calcium carbonate Nutrition 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 235000015424 sodium Nutrition 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000004381 Choline salt Substances 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 235000019417 choline salt Nutrition 0.000 abstract 1
- MQOBSOSZFYZQOK-UHFFFAOYSA-N fenofibric acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 MQOBSOSZFYZQOK-UHFFFAOYSA-N 0.000 abstract 1
- 229960000701 fenofibric acid Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Postupak dobivanja kvaterne amonijeve soli fibrične kiseline formule IV: ,u kojojR1 je atom klora, 2-(4-klorbenzoilamino)etilna skupina, 4-klorbenzoilna skupina ili 2,2-diklorciklopropilna skupinaR2 je nerazgranata ili razgranata C1-C4 alkilna skupina ili nerazgranata ili razgranata C1-C4 hidroksialkilna skupina, R je nerazgranata C1-C3 alkilna skupina, naznačen time što ga se može prikazati sljedećom reakcijskom shemom: te time što ga se provodi u jednom koraku, počevši od fenola formule (I), u kojoj R1 je definiran kao gore, estera formule (II), u kojoj X je halogen, a Ra je nerazgranata ili razgranata C1-C6 alkilna skupina, i kvaternog amonijevog hidroksida formule (III), u kojoj R i R2 su definirani kao gore. Patent sadrži još 9 patentnih zahtjeva.
Claims (10)
1. Postupak dobivanja kvaterne amonijeve soli fibrične kiseline formule IV:
[image]
,
u kojoj
R1 je atom klora, 2-(4-klorbenzoilamino)etilna skupina, 4-klorbenzoilna skupina ili 2,2-diklorciklopropilna skupina
R2 je nerazgranata ili razgranata C1-C4 alkilna skupina ili nerazgranata ili razgranata C1-C4 hidroksialkilna skupina,
R je nerazgranata C1-C3 alkilna skupina,
naznačen time što ga se može prikazati sljedećom reakcijskom shemom:
[image]
te time što ga se provodi u jednom koraku, počevši od fenola formule (I), u kojoj R1 je definiran kao gore, estera formule (II), u kojoj X je halogen, a Ra je nerazgranata ili razgranata C1-C6 alkilna skupina, i kvaternog amonijevog hidroksida formule (III), u kojoj R i R2 su definirani kao gore.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što, u spoju formule (I) danoj gore, R1 se nalazi na para-položaju u odnosu na kisik.
3. Postupak u skladu s patentnim zahtjevom 1 ili 2, naznačen time što, u spoju formule (I) danoj gore, R1 je 4-klorbenzoilna skupina, smještena na para-položaju u odnosu na kisik.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što, u spoju formule (III) danoj gore, R je metilna skupina, a R2 je 2-hidroksietilna skupina.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što, u spoju formule (II) danoj gore, X je atom broma.
6. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što se sastoji u:
– reakciji fenola formule (I) s α-halogeniranim esterom formule (II), kojeg se po mogućnosti upotrebljava u suvišku u odnosu na stehiometrijske uvjete, u prisutnosti baze, na temperaturi između 80 i 160 °C, u trajanju od 1 do 8 sati;
– reakciji kvaternog amonijevog hidroksida formule (III) s dobivenim reakcijskim medijem, u prisutnosti otapala, na temperaturi između 80 i 120 °C, u trajanju od 1 do 5 sati; te
– izdvajanju dobivene soli formule (IV).
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što se sastoji u:
– reakciji fenola formule (I) s α-halogeniranim esterom formule (II), kojeg se po mogućnosti upotrebljava u suvišku u odnosu na stehiometrijske uvjete, u prisutnosti baze, na temperaturi između 80 i 160 °C, u trajanju od 1 do 8 sati;
– reakciji kvaternog amonijevog hidroksida formule (III) s dobivenim reakcijskim medijem, u prisutnosti otapala, po mogućnosti nakon uklanjanja netopivih mineralnih spojeva, na temperaturi između 80 i 120 °C, u trajanju od 1 do 5 sati; te
– izdvajanju dobivene soli formule (IV).
8. Postupak u skladu s patentnim zahtjevom 6 ili 7, naznačen time što se sastoji u:
– reakciji fenola formule (I) s u najmanju ruku stehiometrijski ekvivalentnom količinom estera formule (II), na temperaturi između 80 i 160 °C, u prisutnosti mineralne baze, u trajanju od 1 do 8 sati;
– dodavanju otapala, poput, primjerice, alkohola, u reakcijski medij;
– provođenju vruće filtracije kako bi se uklonilo netopive mineralne spojeve;
– reakciji dobivenog reakcijskog medija s kvaternim amonijevim hidroksidom formule (III), na temperaturi između 80 i 120 °C, u trajanju od 1 do 5 sati; te
– filtraciji vruće smjese, uz naknadno hlađenje u uvjetima koji omogućuju kristalizaciju očekivane soli, nakon čega se kristale odfiltrira i osuši kako bi se dobilo očekivanu sol, čistoće od najmanje 99,5 %.
9. Postupak u skladu s jednim od patentnih zahtjeva 6 do 8, naznačen time što gore navedeno otapalo je nerazgranati ili razgranati propanol.
10. Postupak u skladu s jednim od patentnih zahtjeva 6 do 9, naznačen time što gore navedenu mineralnu bazu se bira između natrijevog ili kalijevog karbonata ili bikarbonata i kalcijevog karbonata.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0511103A FR2892721B1 (fr) | 2005-10-28 | 2005-10-28 | Nouveau procede de preparation de sels d'acides et d'ammonium quaternaires |
| PCT/FR2006/051118 WO2007048986A1 (fr) | 2005-10-28 | 2006-10-27 | Nouveau procede de preparation de sels d'acides et d'ammonium quaternaires |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090514T1 true HRP20090514T1 (hr) | 2010-02-28 |
Family
ID=36699110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090514T HRP20090514T1 (hr) | 2005-10-28 | 2009-09-25 | Novi postupak dobivanja kvaternih kiselih i amonijevih soli |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7714163B2 (hr) |
| EP (1) | EP1940772B1 (hr) |
| JP (1) | JP5069690B2 (hr) |
| CN (1) | CN101296894B (hr) |
| AT (1) | ATE438612T1 (hr) |
| CA (1) | CA2627419C (hr) |
| DE (1) | DE602006008335D1 (hr) |
| DK (1) | DK1940772T3 (hr) |
| EA (1) | EA014027B1 (hr) |
| ES (1) | ES2331337T3 (hr) |
| FR (1) | FR2892721B1 (hr) |
| HK (1) | HK1123275A1 (hr) |
| HR (1) | HRP20090514T1 (hr) |
| IL (1) | IL190399A (hr) |
| PL (1) | PL1940772T3 (hr) |
| PT (1) | PT1940772E (hr) |
| SI (1) | SI1940772T1 (hr) |
| WO (1) | WO2007048986A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITGE20090020A1 (it) * | 2009-04-15 | 2010-10-16 | Chemelectiva | Processo per la sintesi di farmaci |
| WO2016046671A1 (en) * | 2014-09-28 | 2016-03-31 | Mohan M Alapati | Compositions and methods for the treatment of lipid disorders |
| CN109369425B (zh) * | 2018-11-05 | 2022-01-04 | 陕西威信制药有限公司 | 非诺贝特酸胆碱盐的制备方法 |
| CN111138427B (zh) * | 2018-12-05 | 2021-09-17 | 江西富祥药业股份有限公司 | 黄连素及其类似物的非诺贝特酸盐、晶型、制备方法及应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US387486A (en) * | 1888-08-07 | Baling-press | ||
| US3897485A (en) | 1966-10-18 | 1975-07-29 | J Berthier Lab | Choline compounds |
| FR2598146B1 (fr) * | 1986-04-30 | 1989-01-20 | Rech Ind | Nouveau procede de preparation de fibrates. |
| IT1250636B (it) * | 1991-07-04 | 1995-04-21 | Ricerche Di Schiena Del Dr Mic | Sale del diclofenac, metodo di preparazione e composizioni farmaceutiche che lo contengono. |
| ES2109858B1 (es) * | 1994-11-23 | 1998-08-16 | Menarini Lab | Nuevos derivados del acido (+)-(s)-2-(3-benzoilfenil) propionico con accion analgesica y procedimiento para su obtencion. |
| ITMI20010936A1 (it) * | 2001-05-08 | 2002-11-08 | Laboratorio Chimico Int Spa | Processo per la produzione di acidi 2-4-(2,2-dialociclopropil)fenossi|-alcanoici e loro esteri |
| US7259186B2 (en) * | 2002-12-17 | 2007-08-21 | Abbott Laboratories | Salts of fenofibric acid and pharmaceutical formulations thereof |
| US20060148594A1 (en) * | 2005-01-05 | 2006-07-06 | Microsoft Corporation | Smart communicating sports equipment |
-
2005
- 2005-10-28 FR FR0511103A patent/FR2892721B1/fr not_active Expired - Fee Related
-
2006
- 2006-10-27 DK DK06831310T patent/DK1940772T3/da active
- 2006-10-27 ES ES06831310T patent/ES2331337T3/es active Active
- 2006-10-27 DE DE602006008335T patent/DE602006008335D1/de active Active
- 2006-10-27 EA EA200800861A patent/EA014027B1/ru not_active IP Right Cessation
- 2006-10-27 CN CN2006800400281A patent/CN101296894B/zh active Active
- 2006-10-27 JP JP2008537165A patent/JP5069690B2/ja not_active Expired - Fee Related
- 2006-10-27 PL PL06831310T patent/PL1940772T3/pl unknown
- 2006-10-27 PT PT06831310T patent/PT1940772E/pt unknown
- 2006-10-27 SI SI200630443T patent/SI1940772T1/sl unknown
- 2006-10-27 WO PCT/FR2006/051118 patent/WO2007048986A1/fr active Application Filing
- 2006-10-27 AT AT06831310T patent/ATE438612T1/de active
- 2006-10-27 CA CA2627419A patent/CA2627419C/fr not_active Expired - Fee Related
- 2006-10-27 EP EP06831310A patent/EP1940772B1/fr active Active
-
2008
- 2008-03-24 IL IL190399A patent/IL190399A/en active IP Right Grant
- 2008-04-28 US US12/110,667 patent/US7714163B2/en active Active
-
2009
- 2009-01-02 HK HK09100015.2A patent/HK1123275A1/xx unknown
- 2009-09-25 HR HR20090514T patent/HRP20090514T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1123275A1 (en) | 2009-06-12 |
| IL190399A0 (en) | 2008-11-03 |
| DK1940772T3 (da) | 2009-10-26 |
| BRPI0616434A2 (pt) | 2012-12-25 |
| SI1940772T1 (sl) | 2009-12-31 |
| US7714163B2 (en) | 2010-05-11 |
| US20080275270A1 (en) | 2008-11-06 |
| CN101296894B (zh) | 2012-04-04 |
| PT1940772E (pt) | 2009-11-11 |
| DE602006008335D1 (de) | 2009-09-17 |
| EP1940772A1 (fr) | 2008-07-09 |
| JP2009513613A (ja) | 2009-04-02 |
| CA2627419C (fr) | 2014-08-19 |
| EA014027B1 (ru) | 2010-08-30 |
| PL1940772T3 (pl) | 2010-01-29 |
| IL190399A (en) | 2013-07-31 |
| CA2627419A1 (fr) | 2007-05-03 |
| EA200800861A1 (ru) | 2008-10-30 |
| FR2892721A1 (fr) | 2007-05-04 |
| JP5069690B2 (ja) | 2012-11-07 |
| ATE438612T1 (de) | 2009-08-15 |
| WO2007048986A1 (fr) | 2007-05-03 |
| FR2892721B1 (fr) | 2009-07-24 |
| ES2331337T3 (es) | 2009-12-29 |
| CN101296894A (zh) | 2008-10-29 |
| EP1940772B1 (fr) | 2009-08-05 |
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