SK284777B6 - Kryštalická polymorfná forma guajacyl esteru kyseliny 1-metyl-5-p-toluoylpyrol-2-acetaminooctovej a spôsob jej prípravy - Google Patents
Kryštalická polymorfná forma guajacyl esteru kyseliny 1-metyl-5-p-toluoylpyrol-2-acetaminooctovej a spôsob jej prípravy Download PDFInfo
- Publication number
- SK284777B6 SK284777B6 SK895-2000A SK8952000A SK284777B6 SK 284777 B6 SK284777 B6 SK 284777B6 SK 8952000 A SK8952000 A SK 8952000A SK 284777 B6 SK284777 B6 SK 284777B6
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- toluoylpyrrole
- ester
- acetamidoacetic acid
- mixture
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 9
- GZQHOTPDLORUIU-UHFFFAOYSA-N 2-acetamidoacetic acid;(4-methylphenyl)-(1-methylpyrrol-2-yl)methanone Chemical compound CC(=O)NCC(O)=O.C1=CC(C)=CC=C1C(=O)C1=CC=CN1C GZQHOTPDLORUIU-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- CWJNMKKMGIAGDK-UHFFFAOYSA-N amtolmetin guacil Chemical compound COC1=CC=CC=C1OC(=O)CNC(=O)CC(N1C)=CC=C1C(=O)C1=CC=C(C)C=C1 CWJNMKKMGIAGDK-UHFFFAOYSA-N 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
- 229960001017 tolmetin Drugs 0.000 claims description 7
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229960001867 guaiacol Drugs 0.000 claims description 5
- 238000002329 infrared spectrum Methods 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000003814 drug Substances 0.000 description 23
- 229940079593 drug Drugs 0.000 description 23
- 239000000243 solution Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000008298 dragée Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 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
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- -1 1-methyl-5-p-toluoylpyrrole-2-acetoacetic acid Chemical compound 0.000 description 1
- 101100223811 Caenorhabditis elegans dsc-1 gene Proteins 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005280 amorphization Methods 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000009513 drug distribution Methods 0.000 description 1
- VOXANKRFRUBRGI-UHFFFAOYSA-N ethylamino acetate hydrochloride Chemical compound Cl.CCNOC(C)=O VOXANKRFRUBRGI-UHFFFAOYSA-N 0.000 description 1
- 238000011194 good manufacturing practice Methods 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229960002044 tolmetin sodium Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97RM000811A IT1297140B1 (it) | 1997-12-24 | 1997-12-24 | Forma cristallina del guaiacil estere dell'acido l-metil-5-p-toluoil- pirrol-2-acetammidoacetico, procedimento per la sua preparazione e |
| PCT/IT1998/000363 WO1999033797A1 (en) | 1997-12-24 | 1998-12-16 | NEW CRYSTALLINE POLYMORPHIC FORM OF 1-METHYL-5-p-TOLUOYLPYRROLE-2-ACETAMIDOACETIC ACID GUAIACYL ESTER (MED 15) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK8952000A3 SK8952000A3 (en) | 2000-12-11 |
| SK284777B6 true SK284777B6 (sk) | 2005-11-03 |
Family
ID=11405418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK895-2000A SK284777B6 (sk) | 1997-12-24 | 1998-12-16 | Kryštalická polymorfná forma guajacyl esteru kyseliny 1-metyl-5-p-toluoylpyrol-2-acetaminooctovej a spôsob jej prípravy |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6288241B1 (cs) |
| EP (1) | EP1082304B1 (cs) |
| JP (1) | JP4693236B2 (cs) |
| KR (1) | KR100554704B1 (cs) |
| CN (1) | CN1200930C (cs) |
| AT (1) | ATE255562T1 (cs) |
| AU (1) | AU781283B2 (cs) |
| BR (1) | BR9814476A (cs) |
| CA (1) | CA2315835C (cs) |
| CZ (1) | CZ297132B6 (cs) |
| DE (1) | DE69820301T2 (cs) |
| DK (1) | DK1082304T3 (cs) |
| ES (1) | ES2210853T3 (cs) |
| HU (1) | HU228112B1 (cs) |
| IL (1) | IL136828A (cs) |
| IT (1) | IT1297140B1 (cs) |
| PL (1) | PL197768B1 (cs) |
| PT (1) | PT1082304E (cs) |
| SK (1) | SK284777B6 (cs) |
| TR (1) | TR200001867T2 (cs) |
| WO (1) | WO1999033797A1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2020175023A1 (ja) * | 2019-02-28 | 2021-12-16 | 国立大学法人東京工業大学 | アミドの製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1210673B (it) | 1982-02-26 | 1989-09-20 | Medosan Ind Biochimi | Antinfiammatoria amidi pirrolacetiche ad attivita' |
| IT1148117B (it) * | 1982-03-05 | 1986-11-26 | Medosan Ind Biochimi | Attivita'antiflogistica,analgesica,antipiretica,mucolitica e seda tiva della tosse dell'1 metil-5-p-tolilpirrol-2-acetato di 2'metossi-fenile |
| IT1197688B (it) * | 1983-07-29 | 1988-12-06 | Medosan Ind Biochimi | Attivita' antiflogistica,analgesica,antipiretica ed antiaggregante piastrinica di 1-metil-5-metilbenzoilpirrol-2-acetamido acetanilidi |
| IT1278144B1 (it) * | 1995-07-14 | 1997-11-17 | Medosan Ricerca Srl | Impiego dell'amtolmetineguacil (med 15) come farmaco antisecretivo sulla secrezione gastrica e quindi gastroprotettivo. |
| EP1024807B1 (en) * | 1997-08-08 | 2003-04-16 | MEDOSAN RICERCA S.r.l. | Use of the compound 2-methoxyphenyl-1-methyl-5p-methylbenzoyl-pyrrol-2-acetamido acetate for the production of an anti-inflammatory drug with prevention of gastric hypersecretion and renal impairment |
-
1997
- 1997-12-24 IT IT97RM000811A patent/IT1297140B1/it active IP Right Grant
-
1998
- 1998-12-16 ES ES98962664T patent/ES2210853T3/es not_active Expired - Lifetime
- 1998-12-16 DK DK98962664T patent/DK1082304T3/da active
- 1998-12-16 KR KR1020007006998A patent/KR100554704B1/ko not_active Expired - Lifetime
- 1998-12-16 CN CNB988126567A patent/CN1200930C/zh not_active Expired - Lifetime
- 1998-12-16 TR TR2000/01867T patent/TR200001867T2/xx unknown
- 1998-12-16 SK SK895-2000A patent/SK284777B6/sk not_active IP Right Cessation
- 1998-12-16 JP JP2000526481A patent/JP4693236B2/ja not_active Expired - Lifetime
- 1998-12-16 IL IL13682898A patent/IL136828A/xx not_active IP Right Cessation
- 1998-12-16 EP EP98962664A patent/EP1082304B1/en not_active Expired - Lifetime
- 1998-12-16 US US09/581,289 patent/US6288241B1/en not_active Expired - Lifetime
- 1998-12-16 PL PL341424A patent/PL197768B1/pl unknown
- 1998-12-16 BR BR9814476-6A patent/BR9814476A/pt not_active Application Discontinuation
- 1998-12-16 PT PT98962664T patent/PT1082304E/pt unknown
- 1998-12-16 CZ CZ20002336A patent/CZ297132B6/cs not_active IP Right Cessation
- 1998-12-16 HU HU0101025A patent/HU228112B1/hu unknown
- 1998-12-16 DE DE69820301T patent/DE69820301T2/de not_active Expired - Lifetime
- 1998-12-16 WO PCT/IT1998/000363 patent/WO1999033797A1/en active IP Right Grant
- 1998-12-16 AT AT98962664T patent/ATE255562T1/de active
- 1998-12-16 AU AU17828/99A patent/AU781283B2/en not_active Expired
- 1998-12-16 CA CA002315835A patent/CA2315835C/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiry of patent |
Expiry date: 20181216 |