CY1444A - Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production - Google Patents
Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production Download PDFInfo
- Publication number
- CY1444A CY1444A CY1444A CY144489A CY1444A CY 1444 A CY1444 A CY 1444A CY 1444 A CY1444 A CY 1444A CY 144489 A CY144489 A CY 144489A CY 1444 A CY1444 A CY 1444A
- Authority
- CY
- Cyprus
- Prior art keywords
- formula
- dichloroanilino
- hydrogen
- compound
- phenylacetate
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 18
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- -1 2-hydroxypropyl Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 229940049953 phenylacetate Drugs 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 claims description 2
- CHLFQJAVIKSLEU-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetate;morpholin-4-ium Chemical compound C1COCC[NH2+]1.[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl CHLFQJAVIKSLEU-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011369 resultant mixture Substances 0.000 claims description 2
- ZQVZPANTCLRASL-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetate;diethylazanium Chemical compound CCNCC.OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl ZQVZPANTCLRASL-UHFFFAOYSA-N 0.000 claims 1
- NJTLAOVYRDBVEY-UHFFFAOYSA-M 2-[2-(2,6-dichloroanilino)phenyl]acetate;tris(hydroxymethyl)-methylazanium Chemical compound OC[N+](C)(CO)CO.[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl NJTLAOVYRDBVEY-UHFFFAOYSA-M 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 231100000435 percutaneous penetration Toxicity 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- 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
-
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8105822A GB2093693B (en) | 1981-02-24 | 1981-02-24 | Pharmaceutical preparations for topical application which contain salts of alkanecarboxylic acids novel carboxylic acid salts and the production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1444A true CY1444A (en) | 1989-03-10 |
Family
ID=10519933
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1443A CY1443A (en) | 1981-02-24 | 1989-03-10 | Pharmaceutical preparations for topical application which contain salts jof alkanecarboxylic acids,novel carboxylic acid salts and the production thereof |
| CY1444A CY1444A (en) | 1981-02-24 | 1989-03-10 | Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1443A CY1443A (en) | 1981-02-24 | 1989-03-10 | Pharmaceutical preparations for topical application which contain salts jof alkanecarboxylic acids,novel carboxylic acid salts and the production thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US4407824A (en, 2012) |
| AT (1) | AT370721B (en, 2012) |
| CA (1) | CA1180008A (en, 2012) |
| CY (2) | CY1443A (en, 2012) |
| FR (2) | FR2500751A1 (en, 2012) |
| GB (2) | GB2093693B (en, 2012) |
| HK (1) | HK83888A (en, 2012) |
| KE (1) | KE3820A (en, 2012) |
| LU (1) | LU83945A1 (en, 2012) |
| NL (1) | NL193216C (en, 2012) |
| SE (2) | SE448088B (en, 2012) |
| SG (1) | SG33388G (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
| FR2526427A1 (fr) * | 1982-05-04 | 1983-11-10 | Bouchara Emile | Nouveau sel d'indometacine, son procede de preparation et les compositions pharmaceutiques en renfermant |
| US4437053A (en) * | 1982-05-10 | 1984-03-13 | Diasonics (Nmr) Inc. | Gradient power supply |
| CH655656B (en, 2012) * | 1982-10-07 | 1986-05-15 | ||
| ES8407042A1 (es) * | 1982-10-08 | 1984-09-01 | Espinos & Bofill Lab Sa | Procedimiento para la obtencion de un nuevo derivado del sulpiride. |
| JPS59137408A (ja) * | 1983-01-27 | 1984-08-07 | Taisho Pharmaceut Co Ltd | 軟膏 |
| JPS59139315A (ja) * | 1983-01-31 | 1984-08-10 | Taisho Pharmaceut Co Ltd | クリ−ム剤 |
| CH643138A5 (de) * | 1983-08-29 | 1984-05-30 | Mepha Ag | Indomethacin enthaltende, gelartige salbe. |
| DE3381733D1 (de) * | 1983-12-08 | 1990-08-16 | Toko Yakuhin Kogyo Kk | Gelpraeparate zur externen applikation. |
| US4670254A (en) * | 1983-12-09 | 1987-06-02 | Toko Yakuhin Industry Co., Ltd. | Gel preparations for topical application of diclofenac sodium |
| DE3423589A1 (de) * | 1984-06-27 | 1986-01-09 | Wella Ag, 6100 Darmstadt | Oxidationshaarfaerbemittel auf basis einer niedrigviskosen traegermasse |
| IT1178411B (it) * | 1984-09-06 | 1987-09-09 | Sigma Tau Ind Farmaceuti | Sale di d,l-lisina dell'acido 1-(4-clorobenzoil)-5-metossi-2-metil-1h-indol-3 acetico, procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono |
| CA1265288A (en) * | 1984-11-22 | 1990-01-30 | E. I. Du Pont De Nemours And Company | Curable fluoroelastomer composition |
| US4980084A (en) * | 1985-09-11 | 1990-12-25 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Water rinsable petroleum jelly compositions |
| US4690774A (en) * | 1985-09-11 | 1987-09-01 | Chesebrough Pond's Inc. | Novel translucent water in oil emulsions |
| US4832858A (en) * | 1987-02-19 | 1989-05-23 | Chesebrough-Pond's Inc. | Water dispersible petroleum jelly compositions |
| US4960892A (en) * | 1988-06-10 | 1990-10-02 | American Home Products Corporation | Naphthalenepropionic acid derivatives as anti-inflammatory/anti-allergic agents |
| TW225536B (en, 2012) * | 1990-08-23 | 1994-06-21 | Ciba Geigy Ag | |
| US5444076A (en) * | 1990-11-26 | 1995-08-22 | Roemmers S.A.I.C.F. | Pharmaceutical preparation for topical application |
| AU2259692A (en) * | 1991-07-03 | 1993-02-11 | Sano Corporation | Composition and method for transdermal delivery of diclofenac |
| US6117907A (en) * | 1993-04-14 | 2000-09-12 | Sher; Neal A. | Topical treatment of ocular pain after corneal surgery |
| JP3526887B2 (ja) * | 1993-04-23 | 2004-05-17 | 帝國製薬株式会社 | 消炎鎮痛外用貼付剤 |
| FI100692B (fi) * | 1994-05-24 | 1998-02-13 | Leiras Oy | Menetelmä farmaseuttisten koostumusten valmistamiseksi, jolloin koostu mukset pohjautuvat mikroemulsiogeeleihin sekä uusia mikroemulsioihin p ohjautuvia geelejä |
| ATE178884T1 (de) * | 1994-06-29 | 1999-04-15 | Novartis Erfind Verwalt Gmbh | Salze von 2-((2,6- dichlorophenyl)amin>phenylacetoxyessigsäure mit organischen basischen kationen |
| RU2128989C1 (ru) * | 1997-03-05 | 1999-04-20 | Закрытое акционерное общество "Химмедсинтез" | Композиция антимикробного, противовоспалительного и регенерационного действия |
| US20030060657A1 (en) * | 1998-04-28 | 2003-03-27 | Russinsky Limited | Process for the preparation of Aceclofenac |
| RU2177314C2 (ru) * | 2000-03-22 | 2001-12-27 | Кривошеин Юрий Семенович | Состав с антисептическими, репаративными и болеутоляющими свойствами |
| TWI290464B (en) | 2000-09-01 | 2007-12-01 | Novartis Consumer Health Sa | Treatment of burns |
| DE10114561A1 (de) * | 2001-03-24 | 2002-09-26 | Wella Ag | Verwendung von Mitteln enthaltend Kreatin, Kreatin und/oder deren Derivaten zur Verstärkung und Strukturverbesserung von keratinischen Fasern |
| ITMI20020986A1 (it) * | 2002-05-10 | 2003-11-10 | Acraf | Composizione a base di diclofenac per il trattamento topico di affezioni del cavo orofaringeo |
| AR042206A1 (es) | 2002-11-26 | 2005-06-15 | Novartis Ag | Acidos fenilaceticos y derivados |
| ITMI20030269A1 (it) * | 2003-02-14 | 2004-08-15 | Advance Holdings Ltd | Sale di cetilpiridino di un agente antiinfiammatorio |
| FR2854802B1 (fr) * | 2003-05-12 | 2005-06-24 | Galderma Res & Dev | Procede de preparation d'une formulation contenant un principe actif microdose |
| EP2055298A1 (en) | 2007-10-30 | 2009-05-06 | Novartis AG | Topical composition |
| US11000495B2 (en) | 2014-09-10 | 2021-05-11 | GSK Consumer Healthcare S.A. | Topical diclofenac sodium compositions |
| CN116143647A (zh) * | 2023-03-03 | 2023-05-23 | 长沙晶易医药科技股份有限公司 | 双氯芬酸二乙胺的新晶型及其制备方法 |
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| US514839A (en) * | 1894-02-13 | sergeant | ||
| GB971700A (en) * | 1961-02-02 | 1964-09-30 | Boots Pure Drug Co Ltd | Anti-Inflammatory Agents |
| AT290523B (de) * | 1962-01-05 | 1971-06-11 | Merck & Co Inc | Verfahren zur Herstellung neuer α-(3-Indolyl)-carbonsäuren |
| US3558690A (en) * | 1965-04-08 | 1971-01-26 | Gelgy Chemical Corp | Substituted derivatives of 2-anilinophenylacetic acids and a process of preparation |
| CH470349A (de) * | 1966-10-07 | 1969-03-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
| US3896157A (en) * | 1967-01-13 | 1975-07-22 | Syntex Corp | Dihydo 2-naphthylacetic acid derivatives |
| US4048330A (en) * | 1967-01-13 | 1977-09-13 | Syntex Corporation | Compositions containing 2-(6'-substituted-2'-naphthyl)acetic acid esters used for treating inflammation, pain or pyrexia |
| CA960689A (en) * | 1967-01-13 | 1975-01-07 | Syntex Corporation | 2-naphthyl acetic acid derivatives and compositions |
| FR1546478A (fr) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
| US3592902A (en) * | 1967-04-13 | 1971-07-13 | Sumitomo Chemical Co | Injection |
| NL6817965A (en, 2012) * | 1967-12-20 | 1969-06-24 | ||
| US3641040A (en) * | 1968-03-27 | 1972-02-08 | Ciba Geigy Corp | Tertiary amino phenyl acetic acids |
| US3637767A (en) * | 1968-07-30 | 1972-01-25 | Syntex Corp | 2-(6'-methoxynaphth-2'-yl)propylene oxide and 5'-halo derivatives |
| BR6915470D0 (pt) * | 1969-03-24 | 1973-03-13 | Syntex Corp | Processo para preparar derivados de acido 2-(6'substituido 2'naftil)propionico e de seus sais |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| US3647858A (en) * | 1970-05-01 | 1972-03-07 | Merck & Co Inc | Process for preparing 1-benzylidene-3-indenyl acetic acids |
| US4033816A (en) | 1973-06-18 | 1977-07-05 | The Upjohn Company | Process for inhibiting platelet aggregation |
| US3936528A (en) * | 1974-02-13 | 1976-02-03 | Syntex Corporation | Analgesic formulations having enhanced therapeutic activity |
| ES423834A1 (es) * | 1974-03-02 | 1976-06-01 | Roger Lab | Procedimiento de obtencion de una nueva sal de piperacina del acido (1 - p - clorobenzoil - 2 - metil - 5 - metoxi - 3- indolil) acetico. |
| US4031243A (en) * | 1975-07-03 | 1977-06-21 | Juste, S.A. Quimico-Farmaceutica | 2-(4-Isobutyl phenyl)butyric acid, salts thereof, and pharmaceutical compositions containing the same |
| PT66660B (en) * | 1976-06-12 | 1978-11-13 | Ciba Geigy Ag | Process for the production of a derivative of phenylacetic |
| LU77316A1 (en, 2012) * | 1977-05-11 | 1979-01-19 | ||
| JPS549240A (en) * | 1977-06-23 | 1979-01-24 | Asahi Chem Ind Co Ltd | New derivative of phenylglycolic acid, its preparation and analgesic and antiinflammatory agent contining it as effective component |
| GB2023000B (en) * | 1978-06-17 | 1982-10-13 | Kowa Co | Antinflammatory analgesic gelled ointments |
| BE871335A (fr) * | 1978-10-18 | 1979-04-18 | Bago Sa Labor | Derives solubles des acides 2-anilino-aryl-carboxyliques substitues utiles par la voie buccale comme agents anti-inflammatoires. |
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
-
1981
- 1981-02-16 AT AT0070981A patent/AT370721B/de not_active IP Right Cessation
- 1981-02-17 SE SE8101064A patent/SE448088B/sv not_active IP Right Cessation
- 1981-02-19 CA CA000371271A patent/CA1180008A/en not_active Expired
- 1981-02-20 US US06/236,097 patent/US4407824A/en not_active Expired - Lifetime
- 1981-02-24 GB GB8105822A patent/GB2093693B/en not_active Expired
- 1981-02-25 NL NL8100917A patent/NL193216C/nl not_active IP Right Cessation
- 1981-02-27 FR FR8103932A patent/FR2500751A1/fr active Granted
- 1981-10-09 FR FR8119055A patent/FR2514348A1/fr active Granted
-
1982
- 1982-02-15 LU LU83945A patent/LU83945A1/de unknown
- 1982-05-25 SE SE8203228A patent/SE8203228L/xx unknown
-
1983
- 1983-07-27 US US06/517,606 patent/US4551475A/en not_active Expired - Lifetime
-
1984
- 1984-07-16 GB GB08418021A patent/GB2143528B/en not_active Expired
-
1985
- 1985-08-14 US US06/765,416 patent/US4619926A/en not_active Expired - Lifetime
-
1988
- 1988-02-18 US US07/156,770 patent/US4784808A/en not_active Expired - Lifetime
- 1988-05-27 SG SG33388A patent/SG33388G/en unknown
- 1988-06-07 KE KE3820A patent/KE3820A/xx unknown
- 1988-10-13 HK HK838/88A patent/HK83888A/xx not_active IP Right Cessation
-
1989
- 1989-03-10 CY CY1443A patent/CY1443A/en unknown
- 1989-03-10 CY CY1444A patent/CY1444A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2143528B (en) | 1985-10-02 |
| SE8203228L (sv) | 1982-08-18 |
| GB2093693B (en) | 1985-10-02 |
| SG33388G (en) | 1988-09-30 |
| FR2500751B1 (en, 2012) | 1984-12-28 |
| ATA70981A (de) | 1982-09-15 |
| FR2514348A1 (fr) | 1983-04-15 |
| KE3820A (en) | 1988-09-09 |
| US4407824A (en) | 1983-10-04 |
| CA1180008A (en) | 1984-12-27 |
| US4619926A (en) | 1986-10-28 |
| FR2514348B1 (en, 2012) | 1984-12-14 |
| NL8100917A (nl) | 1982-09-16 |
| AT370721B (de) | 1983-04-25 |
| NL193216B (nl) | 1998-11-02 |
| HK83888A (en) | 1988-10-21 |
| FR2500751A1 (fr) | 1982-09-03 |
| US4551475A (en) | 1985-11-05 |
| GB2143528A (en) | 1985-02-13 |
| GB8418021D0 (en) | 1984-08-22 |
| NL193216C (nl) | 1999-03-03 |
| LU83945A1 (de) | 1982-12-13 |
| SE8101064L (sv) | 1982-08-18 |
| CY1443A (en) | 1989-03-10 |
| GB2093693A (en) | 1982-09-08 |
| US4784808A (en) | 1988-11-15 |
| SE448088B (sv) | 1987-01-19 |
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