CA1062280A - Procede de preparation de clofibrate de metformine - Google Patents
Procede de preparation de clofibrate de metformineInfo
- Publication number
- CA1062280A CA1062280A CA222,798A CA222798A CA1062280A CA 1062280 A CA1062280 A CA 1062280A CA 222798 A CA222798 A CA 222798A CA 1062280 A CA1062280 A CA 1062280A
- Authority
- CA
- Canada
- Prior art keywords
- metformin
- clofibrate
- salt
- acid
- preparation
- 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.)
- Expired
Links
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 title claims abstract description 32
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 title claims description 13
- 229960001214 clofibrate Drugs 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229960003105 metformin Drugs 0.000 claims abstract description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 229960004329 metformin hydrochloride Drugs 0.000 claims description 5
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 13
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 abstract description 11
- 229950008441 clofibric acid Drugs 0.000 abstract description 11
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 abstract description 10
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 3
- 230000002641 glycemic effect Effects 0.000 abstract description 2
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 2
- 230000002792 vascular Effects 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CKJRQPWAXMFUCK-UHFFFAOYSA-N methane;propan-2-one Chemical compound C.CC(C)=O CKJRQPWAXMFUCK-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7409963A FR2264525B1 (cs) | 1974-03-22 | 1974-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062280A true CA1062280A (fr) | 1979-09-11 |
Family
ID=9136732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA222,798A Expired CA1062280A (fr) | 1974-03-22 | 1975-03-21 | Procede de preparation de clofibrate de metformine |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5526134B2 (cs) |
| AT (1) | AT346856B (cs) |
| BE (1) | BE826999A (cs) |
| CA (1) | CA1062280A (cs) |
| CH (1) | CH609669A5 (cs) |
| DE (1) | DE2511576C2 (cs) |
| ES (1) | ES435898A1 (cs) |
| FR (1) | FR2264525B1 (cs) |
| GB (1) | GB1462316A (cs) |
| LU (1) | LU72102A1 (cs) |
| NL (1) | NL169461C (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2774591B1 (fr) * | 1998-02-12 | 2000-05-05 | Lipha | Composition pharmaceutique comprenant l'association metformine et fibrate et son utilisation pour la preparation de medicaments destines a reduire l'hyperglycemie |
| FR2796551B1 (fr) * | 1999-07-23 | 2003-07-25 | Lipha | Nouveaux sels de metformine, leur procede d'obtention et les compositions pharmaceutiques en renfermant |
| FR2796940B1 (fr) * | 1999-07-26 | 2005-04-08 | Lipha | Nouveaux sels de metformine, leur procede d'obtention et les compositions pharmaceutiques en renfermant |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR7116M (cs) * | 1968-01-08 | 1969-07-15 | ||
| AT317235B (de) * | 1972-08-22 | 1974-08-26 | Hurka Wilhelm | Verfahren zur Herstellung des neuen 2-(p-Chlorphenoxy)-2-methylpropionsäuresalzes des 1-Phenäthylbiguanids |
-
1974
- 1974-03-22 FR FR7409963A patent/FR2264525B1/fr not_active Expired
-
1975
- 1975-03-17 DE DE2511576A patent/DE2511576C2/de not_active Expired
- 1975-03-20 LU LU72102A patent/LU72102A1/xx unknown
- 1975-03-21 ES ES435898A patent/ES435898A1/es not_active Expired
- 1975-03-21 AT AT217875A patent/AT346856B/de not_active IP Right Cessation
- 1975-03-21 BE BE154602A patent/BE826999A/xx unknown
- 1975-03-21 CA CA222,798A patent/CA1062280A/fr not_active Expired
- 1975-03-21 GB GB1199975A patent/GB1462316A/en not_active Expired
- 1975-03-21 CH CH362775A patent/CH609669A5/xx not_active IP Right Cessation
- 1975-03-22 JP JP3484475A patent/JPS5526134B2/ja not_active Expired
- 1975-03-24 NL NLAANVRAGE7503515,A patent/NL169461C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES435898A1 (es) | 1976-12-16 |
| AT346856B (de) | 1978-11-27 |
| FR2264525A1 (cs) | 1975-10-17 |
| NL169461B (nl) | 1982-02-16 |
| BE826999A (fr) | 1975-07-16 |
| LU72102A1 (cs) | 1975-08-20 |
| ATA217875A (de) | 1978-04-15 |
| JPS5526134B2 (cs) | 1980-07-11 |
| NL169461C (nl) | 1982-07-16 |
| CH609669A5 (en) | 1979-03-15 |
| JPS50135043A (cs) | 1975-10-25 |
| FR2264525B1 (cs) | 1977-11-04 |
| DE2511576C2 (de) | 1983-07-07 |
| DE2511576A1 (de) | 1975-09-25 |
| GB1462316A (en) | 1977-01-26 |
| NL7503515A (nl) | 1975-09-24 |
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