HU194877B - Process for producing morpholinoethyl-ester-diniflumate of nifluminic acid and pharmaceutical composition containing them - Google Patents
Process for producing morpholinoethyl-ester-diniflumate of nifluminic acid and pharmaceutical composition containing them Download PDFInfo
- Publication number
- HU194877B HU194877B HU841552A HU155284A HU194877B HU 194877 B HU194877 B HU 194877B HU 841552 A HU841552 A HU 841552A HU 155284 A HU155284 A HU 155284A HU 194877 B HU194877 B HU 194877B
- Authority
- HU
- Hungary
- Prior art keywords
- morpholinoethyl
- compound
- diniflumate
- ester
- pharmaceutical composition
- Prior art date
Links
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 229960000916 niflumic acid Drugs 0.000 title description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- -1 morpholinoethyl ester Chemical class 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 description 15
- 231100000397 ulcer Toxicity 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 206010030113 Oedema Diseases 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- LDXSPUSKBDTEKA-UHFFFAOYSA-N morniflumate Chemical compound FC(F)(F)C1=CC=CC(NC=2C(=CC=CN=2)C(=O)OCCN2CCOCC2)=C1 LDXSPUSKBDTEKA-UHFFFAOYSA-N 0.000 description 5
- 229960003251 morniflumate Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001760 anti-analgesic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- FYBLYUCJZSTSKR-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(NC=2C(=CC=CN=2)C(=O)OCCN2CCOCC2)=C1 FYBLYUCJZSTSKR-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8306579A FR2544718B1 (fr) | 1983-04-21 | 1983-04-21 | Diniflumate d'ester morpholinoethylique d'acide niflumique, preparation, utilisation en therapeutique comme analgesique et anti-inflammatoire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT34188A HUT34188A (en) | 1985-02-28 |
| HU194877B true HU194877B (en) | 1988-03-28 |
Family
ID=9288097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841552A HU194877B (en) | 1983-04-21 | 1984-04-20 | Process for producing morpholinoethyl-ester-diniflumate of nifluminic acid and pharmaceutical composition containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4595686A (enExample) |
| EP (1) | EP0129449B1 (enExample) |
| JP (1) | JPS59199676A (enExample) |
| KR (1) | KR880001477B1 (enExample) |
| AR (1) | AR240314A1 (enExample) |
| AT (1) | ATE33639T1 (enExample) |
| AU (1) | AU561210B2 (enExample) |
| CA (1) | CA1218064A (enExample) |
| DE (1) | DE3470534D1 (enExample) |
| DK (1) | DK157858C (enExample) |
| EG (1) | EG17886A (enExample) |
| ES (1) | ES8502111A1 (enExample) |
| FR (1) | FR2544718B1 (enExample) |
| GB (1) | GB2140008B (enExample) |
| GR (1) | GR81476B (enExample) |
| HU (1) | HU194877B (enExample) |
| IE (1) | IE57219B1 (enExample) |
| IL (1) | IL71525A (enExample) |
| MA (1) | MA20097A1 (enExample) |
| MY (1) | MY100483A (enExample) |
| NZ (1) | NZ207913A (enExample) |
| PH (1) | PH18986A (enExample) |
| PT (1) | PT78432B (enExample) |
| SG (1) | SG107587G (enExample) |
| YU (1) | YU65784A (enExample) |
| ZA (1) | ZA842672B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5192724A (en) * | 1992-03-17 | 1993-03-09 | Phillips Petroleum Company | Reactivation of spent cracking catalysts |
| GB0006897D0 (en) * | 2000-03-23 | 2000-05-10 | Smithkline Beecham Plc | Medicaments |
| CA2450073C (en) | 2001-07-25 | 2017-08-29 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| EP2671508B1 (en) | 2005-04-28 | 2020-09-16 | Proteus Digital Health, Inc. | Pharma-informatics system |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| ES2919563T3 (es) | 2009-02-20 | 2022-07-27 | Enhanx Biopharm Inc | Sistema de administración de medicamentos a base de glutatión |
| KR20180114970A (ko) | 2009-05-06 | 2018-10-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US27822A (en) * | 1860-04-10 | Isaac mott | ||
| GB1146459A (en) * | 1966-11-14 | 1969-03-26 | American Cyanamid Co | Nicotinic acid derivatives and method of preparing the same |
| GB1187259A (en) * | 1967-10-23 | 1970-04-08 | Hexachimie | New Aminoalkyl Esters of 2-Anilino-Nicotinic Acids and process for their manufacture |
| USRE27822E (en) | 1971-07-06 | 1973-11-27 | Substituted phenoxy-z-hydroxy- j-isopropylamino-propanes | |
| DE2601548C2 (de) * | 1976-01-16 | 1984-01-26 | Hoechst Ag, 6230 Frankfurt | 2-[4-(2'-Chlor-4'-bromphenoxy)-phenoxy]-propionsäure und Derivate sowie diese enthaltende herbizide Mittel |
| AR208619A1 (es) * | 1976-09-02 | 1977-02-15 | Bago Sa Labor | Un procedimiento para la obtencion de 2(3'-trifluormetilanilino)nicotinato de 5-hidroxi-6-metil-3,4-piridina dimetano |
| US4386090A (en) * | 1980-12-22 | 1983-05-31 | Delalande S.A. | Nitrogen containing 2,3-dihydro naphthalenes, compositions and use |
| IT1150194B (it) * | 1982-02-23 | 1986-12-10 | Chiesi Farma Spa | Formulazioni farmaceutiche ad attivita'antiinfiammatoria, analgesica,antipiretica e gastroprotettiva |
-
1983
- 1983-04-21 FR FR8306579A patent/FR2544718B1/fr not_active Expired
-
1984
- 1984-04-05 IE IE843/84A patent/IE57219B1/xx unknown
- 1984-04-09 US US06/597,808 patent/US4595686A/en not_active Expired - Fee Related
- 1984-04-09 GB GB08409104A patent/GB2140008B/en not_active Expired
- 1984-04-10 YU YU00657/84A patent/YU65784A/xx unknown
- 1984-04-10 AR AR296242A patent/AR240314A1/es active
- 1984-04-11 AU AU26748/84A patent/AU561210B2/en not_active Ceased
- 1984-04-11 ZA ZA842672A patent/ZA842672B/xx unknown
- 1984-04-12 IL IL71525A patent/IL71525A/xx unknown
- 1984-04-17 PT PT78432A patent/PT78432B/pt not_active IP Right Cessation
- 1984-04-17 CA CA000452208A patent/CA1218064A/en not_active Expired
- 1984-04-17 ES ES531679A patent/ES8502111A1/es not_active Expired
- 1984-04-18 PH PH30587A patent/PH18986A/en unknown
- 1984-04-18 GR GR74463A patent/GR81476B/el unknown
- 1984-04-18 DK DK200884A patent/DK157858C/da not_active IP Right Cessation
- 1984-04-19 NZ NZ207913A patent/NZ207913A/en unknown
- 1984-04-19 KR KR1019840002063A patent/KR880001477B1/ko not_active Expired
- 1984-04-19 JP JP59077626A patent/JPS59199676A/ja active Pending
- 1984-04-20 DE DE8484400813T patent/DE3470534D1/de not_active Expired
- 1984-04-20 AT AT84400813T patent/ATE33639T1/de not_active IP Right Cessation
- 1984-04-20 EP EP84400813A patent/EP0129449B1/fr not_active Expired
- 1984-04-20 MA MA20318A patent/MA20097A1/fr unknown
- 1984-04-20 HU HU841552A patent/HU194877B/hu not_active IP Right Cessation
- 1984-04-21 EG EG252/84A patent/EG17886A/xx active
-
1987
- 1987-10-01 MY MYPI87002704A patent/MY100483A/en unknown
- 1987-12-08 SG SG1075/87A patent/SG107587G/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |