DE2541475A1 - Neue derivate der acetylsalicylsaeure, deren herstellung und diese enthaltende zusammensetzungen - Google Patents
Neue derivate der acetylsalicylsaeure, deren herstellung und diese enthaltende zusammensetzungenInfo
- Publication number
- DE2541475A1 DE2541475A1 DE19752541475 DE2541475A DE2541475A1 DE 2541475 A1 DE2541475 A1 DE 2541475A1 DE 19752541475 DE19752541475 DE 19752541475 DE 2541475 A DE2541475 A DE 2541475A DE 2541475 A1 DE2541475 A1 DE 2541475A1
- Authority
- DE
- Germany
- Prior art keywords
- acetylsalicylic acid
- compositions
- alkyl radical
- carbon atoms
- general formula
- 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.)
- Pending
Links
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical class CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 18
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYHKIJRBQSAXGS-UHFFFAOYSA-N 2-acetyloxybenzoic acid;2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O.CC(=O)OC1=CC=CC=C1C(O)=O VYHKIJRBQSAXGS-UHFFFAOYSA-N 0.000 description 3
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- -1 aminoacetamide acetyl salicylate Chemical compound 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- OPSUSMMZNXNXKD-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropanamide Chemical compound CN(C)C(C)(C)C(N)=O OPSUSMMZNXNXKD-UHFFFAOYSA-N 0.000 description 2
- FTJJDCJLMLWWPS-UHFFFAOYSA-N 2-amino-2,4-dimethylpentanamide Chemical compound CC(C)CC(C)(N)C(N)=O FTJJDCJLMLWWPS-UHFFFAOYSA-N 0.000 description 2
- YLYOSYIKDVALRB-UHFFFAOYSA-N 2-amino-2-methylbutanamide Chemical compound CCC(C)(N)C(N)=O YLYOSYIKDVALRB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- GQEXBJOPGJUKIL-UHFFFAOYSA-N 1-aminocyclohexane-1-carboxamide Chemical compound NC(=O)C1(N)CCCCC1 GQEXBJOPGJUKIL-UHFFFAOYSA-N 0.000 description 1
- TXHAIUDPXPETQH-UHFFFAOYSA-N 2-acetyloxybenzoic acid 1-aminocyclohexane-1-carboxamide Chemical compound C(C)(=O)OC=1C(C(=O)O)=CC=CC1.NC1(CCCCC1)C(=O)N TXHAIUDPXPETQH-UHFFFAOYSA-N 0.000 description 1
- ISEGNDGYFDXQBZ-UHFFFAOYSA-N 2-acetyloxybenzoic acid 2-(dimethylamino)-2-methylpropanamide Chemical compound C(C)(=O)OC=1C(C(=O)O)=CC=CC1.CN(C(C(=O)N)(C)C)C ISEGNDGYFDXQBZ-UHFFFAOYSA-N 0.000 description 1
- ZKZFXESBOZEATG-UHFFFAOYSA-N 2-acetyloxybenzoic acid 2-amino-2-methylbutanamide Chemical compound C(C)(=O)OC=1C(C(=O)O)=CC=CC1.NC(C(=O)N)(CC)C ZKZFXESBOZEATG-UHFFFAOYSA-N 0.000 description 1
- YTSVIBZGAFTNCI-UHFFFAOYSA-N 2-methyl-2-(methylamino)propanamide Chemical compound CNC(C)(C)C(N)=O YTSVIBZGAFTNCI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- PSHLPPZDZLDIQT-UHFFFAOYSA-N C(C)(=O)OC=1C(C(=O)O)=CC=CC1.C(N)(=O)C1NCCCC1 Chemical compound C(C)(=O)OC=1C(C(=O)O)=CC=CC1.C(N)(=O)C1NCCCC1 PSHLPPZDZLDIQT-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229940068372 acetyl salicylate Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7431400A FR2285141A1 (fr) | 1974-09-17 | 1974-09-17 | Nouveau derive de l'acide acetylsalicylique, sa preparation et les compositions qui le contiennent |
| FR7520099A FR2315279A1 (fr) | 1975-06-26 | 1975-06-26 | Nouveaux derives de l'acide acetylsalicylique, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2541475A1 true DE2541475A1 (de) | 1976-03-25 |
Family
ID=26218517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752541475 Pending DE2541475A1 (de) | 1974-09-17 | 1975-09-17 | Neue derivate der acetylsalicylsaeure, deren herstellung und diese enthaltende zusammensetzungen |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5161615A (en, 2012) |
| AT (1) | AT339886B (en, 2012) |
| AU (1) | AU8484975A (en, 2012) |
| CH (1) | CH593234A5 (en, 2012) |
| DE (1) | DE2541475A1 (en, 2012) |
| ES (1) | ES441029A1 (en, 2012) |
| FI (1) | FI752589A7 (en, 2012) |
| GB (1) | GB1476026A (en, 2012) |
| HU (1) | HU172524B (en, 2012) |
| IL (1) | IL48108A0 (en, 2012) |
| LU (1) | LU73412A1 (en, 2012) |
| NL (1) | NL7510622A (en, 2012) |
| NO (1) | NO753158L (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3036367A1 (de) * | 1979-09-27 | 1981-04-16 | Kahan Ilona | Wasserloesliche derivate von nichtsteroiden entzuendungshemmenden mitteln, und verfahren zur herstellung solcher derivate, sowie solche derivate enthaltende therapheutische zubereitungen |
| DE3105908A1 (de) * | 1980-08-29 | 1982-04-15 | Laboratorios Bago S.A., Buenos Aires | Substituierte benzoesaeureester und deren zwischenprodukte, verfahren zu ihrer herstellung und pharmazeutische zubereitungen |
-
1975
- 1975-09-09 NL NL7510622A patent/NL7510622A/xx not_active Application Discontinuation
- 1975-09-15 AU AU84849/75A patent/AU8484975A/en not_active Expired
- 1975-09-15 HU HU75RO00000854A patent/HU172524B/hu unknown
- 1975-09-16 JP JP50111023A patent/JPS5161615A/ja active Pending
- 1975-09-16 NO NO753158A patent/NO753158L/no unknown
- 1975-09-16 CH CH1197375A patent/CH593234A5/xx not_active IP Right Cessation
- 1975-09-16 LU LU73412A patent/LU73412A1/xx unknown
- 1975-09-16 IL IL48108A patent/IL48108A0/xx unknown
- 1975-09-17 ES ES441029A patent/ES441029A1/es not_active Expired
- 1975-09-17 AT AT713675A patent/AT339886B/de active
- 1975-09-17 DE DE19752541475 patent/DE2541475A1/de active Pending
- 1975-09-17 FI FI752589A patent/FI752589A7/fi not_active Application Discontinuation
- 1975-09-17 GB GB3823075A patent/GB1476026A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3036367A1 (de) * | 1979-09-27 | 1981-04-16 | Kahan Ilona | Wasserloesliche derivate von nichtsteroiden entzuendungshemmenden mitteln, und verfahren zur herstellung solcher derivate, sowie solche derivate enthaltende therapheutische zubereitungen |
| DE3105908A1 (de) * | 1980-08-29 | 1982-04-15 | Laboratorios Bago S.A., Buenos Aires | Substituierte benzoesaeureester und deren zwischenprodukte, verfahren zu ihrer herstellung und pharmazeutische zubereitungen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1476026A (en) | 1977-06-10 |
| AT339886B (de) | 1977-11-10 |
| AU8484975A (en) | 1977-03-24 |
| NL7510622A (nl) | 1976-03-19 |
| JPS5161615A (en, 2012) | 1976-05-28 |
| NO753158L (en, 2012) | 1976-03-18 |
| CH593234A5 (en, 2012) | 1977-11-30 |
| HU172524B (hu) | 1978-09-28 |
| ES441029A1 (es) | 1977-03-01 |
| IL48108A0 (en) | 1975-11-25 |
| ATA713675A (de) | 1977-03-15 |
| LU73412A1 (en, 2012) | 1976-08-13 |
| FI752589A7 (en, 2012) | 1976-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |