SE448991B - Analogiforfarande for framstellning av n-acetyl-para-aminofenyl-n'acetyl-d,l-metionat som har analgetisk aktivitet - Google Patents
Analogiforfarande for framstellning av n-acetyl-para-aminofenyl-n'acetyl-d,l-metionat som har analgetisk aktivitetInfo
- Publication number
- SE448991B SE448991B SE7806038A SE7806038A SE448991B SE 448991 B SE448991 B SE 448991B SE 7806038 A SE7806038 A SE 7806038A SE 7806038 A SE7806038 A SE 7806038A SE 448991 B SE448991 B SE 448991B
- Authority
- SE
- Sweden
- Prior art keywords
- acetyl
- para
- napa
- aminophenyl
- compound
- Prior art date
Links
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- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 229960001051 dimercaprol Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- PNDDHEORJIOXJT-UHFFFAOYSA-L disodium dodecyl sulfate hydrogen carbonate Chemical compound [Na+].[Na+].OC([O-])=O.CCCCCCCCCCCCOS([O-])(=O)=O PNDDHEORJIOXJT-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229940099459 n-acetylmethionine Drugs 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
- MMMNTDFSPSQXJP-UHFFFAOYSA-N orphenadrine citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 MMMNTDFSPSQXJP-UHFFFAOYSA-N 0.000 description 1
- 229960001687 orphenadrine citrate Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 229960005382 phenolphthalein Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PXWLVJLKJGVOKE-UHFFFAOYSA-N propyphenazone Chemical compound O=C1C(C(C)C)=C(C)N(C)N1C1=CC=CC=C1 PXWLVJLKJGVOKE-UHFFFAOYSA-N 0.000 description 1
- 229960002189 propyphenazone Drugs 0.000 description 1
- 208000018299 prostration Diseases 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 229960003447 pseudoephedrine hydrochloride Drugs 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 108060007951 sulfatase Proteins 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22218/77A GB1583602A (en) | 1977-05-26 | 1977-05-26 | N-acetyl-para-aminophenyl-n'-acetyl-amino-thioalkanoic acid ester derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7806038L SE7806038L (sv) | 1978-11-27 |
| SE448991B true SE448991B (sv) | 1987-03-30 |
Family
ID=10175844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7806038A SE448991B (sv) | 1977-05-26 | 1978-05-25 | Analogiforfarande for framstellning av n-acetyl-para-aminofenyl-n'acetyl-d,l-metionat som har analgetisk aktivitet |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US4181719A (de) |
| AT (1) | AT368489B (de) |
| BE (1) | BE867531A (de) |
| CH (1) | CH644590A5 (de) |
| DE (1) | DE2822789C2 (de) |
| DK (1) | DK155832C (de) |
| FI (1) | FI70208C (de) |
| FR (1) | FR2391998A1 (de) |
| GB (1) | GB1583602A (de) |
| IE (1) | IE47072B1 (de) |
| IT (1) | IT1202822B (de) |
| LU (1) | LU79703A1 (de) |
| NL (1) | NL176070C (de) |
| NO (1) | NO146392C (de) |
| SE (1) | SE448991B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1111384B (it) * | 1978-12-21 | 1986-01-13 | Sigma Tau Ind Farmaceuti | Guaiacil esteri di derivati dello acido mercaptopropionico procedimento per la loro preparazione e loro uso terapeutico |
| US4307073A (en) * | 1980-08-08 | 1981-12-22 | The Research Foundation Of State University Of New York | Method and composition for reducing the toxicity of acetaminophen |
| US4504413A (en) * | 1982-04-02 | 1985-03-12 | Syva Company | Acetaminophen analogs, antigens, and antibodies |
| US4605754A (en) * | 1982-04-02 | 1986-08-12 | Syntex (U.S.A.) Inc. | Acetaminophen analogs |
| US5103021A (en) * | 1982-04-02 | 1992-04-07 | Syntex (U.S.A.) Inc. | Acetaminophen analogs, antigens, and antibodies |
| CH654302A5 (de) * | 1983-05-04 | 1986-02-14 | Sandoz Ag | Acylaminophenolderivate, ihre herstellung und arzneimittel, welche sie enthalten. |
| GB9305058D0 (en) * | 1993-03-12 | 1993-04-28 | Penn Pharm Ltd | Pharmaceutical compositions |
| DE19711053C2 (de) * | 1997-03-03 | 1999-09-02 | Rommelspacher | Kombinationspräparat aus 2-Methyl-thiazolidin-2,4-dicarbonsäure und Paracetamol |
| FR2814366A1 (fr) * | 2000-09-22 | 2002-03-29 | Rhodia Chimie Sa | Procede de granulation de matieres actives par extrusion basse pression pour l'obtention de granules directement compressibles |
| WO2002036077A2 (en) * | 2000-11-06 | 2002-05-10 | Andrx Pharmaceuticals, Inc. | Once a day antihistamine and decongestant formulation |
| GB0114069D0 (en) * | 2001-06-08 | 2001-08-01 | Smithkline Beecham Plc | Composition |
| US8092831B2 (en) * | 2002-11-08 | 2012-01-10 | Andrx Pharmaceuticals, Llc | Antihistamine and decongestant system |
| WO2004045551A2 (en) * | 2002-11-15 | 2004-06-03 | Branded Products For The Future | Pharmaceutical composition |
| US20050220862A1 (en) * | 2004-03-31 | 2005-10-06 | Bernstein Joel E | Compositions with reduced hepatotoxicity |
| WO2009138437A1 (en) * | 2008-05-13 | 2009-11-19 | Genmedica Therapeutics Sl | Salicylate conjugates useful for treating metabolic disorders |
| EP2285419A4 (de) * | 2008-05-20 | 2012-05-02 | Neurogesx Inc | Leberschützende mutuale paracetamol-prodrugs |
| US20100239552A1 (en) * | 2009-03-16 | 2010-09-23 | Genmedica Therapeutics Sl | Combination Therapies for Treating Metabolic Disorders |
| US8575217B2 (en) * | 2009-03-16 | 2013-11-05 | Genmedica Therapeutics Sl | Anti-inflammatory and antioxidant conjugates useful for treating metabolic disorders |
| US8466197B2 (en) | 2010-12-14 | 2013-06-18 | Genmedica Therapeutics Sl | Thiocarbonates as anti-inflammatory and antioxidant compounds useful for treating metabolic disorders |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR462M (de) * | 1958-10-13 | 1961-05-02 | ||
| US3591686A (en) * | 1967-08-01 | 1971-07-06 | Mead Johnson & Co | Anti-inflammatory compositions and methods utilizing n-acylcysteines and the beta-alkyl and carboxyl derivatives thereof |
| US4038306A (en) * | 1967-08-07 | 1977-07-26 | Merck & Co., Inc. | N-t-butoxycarbonyl-s-lower alkanoylamidomethyl-cysteine and p-nitrophenyl esters |
| GB1428803A (en) * | 1973-05-29 | 1976-03-17 | Gallardo Antonio Sa | 4-acetamidophenyl esters of aryl-alkane carboxylic acids and a process for their preparation |
| US3983138A (en) * | 1973-09-25 | 1976-09-28 | Merck & Co., Inc. | Amino acid esters |
| GB1463505A (en) * | 1973-11-21 | 1977-02-02 | Nat Res Dev | Pharmaceutical compositions |
| US3996268A (en) * | 1974-09-03 | 1976-12-07 | The Regents Of The University Of California | Cross-linking reagent for insulin synthesis |
-
1977
- 1977-05-26 GB GB22218/77A patent/GB1583602A/en not_active Expired
-
1978
- 1978-05-22 FI FI781610A patent/FI70208C/fi not_active IP Right Cessation
- 1978-05-24 DE DE2822789A patent/DE2822789C2/de not_active Expired
- 1978-05-24 AT AT0380178A patent/AT368489B/de not_active IP Right Cessation
- 1978-05-25 NL NLAANVRAGE7805675,A patent/NL176070C/xx not_active IP Right Cessation
- 1978-05-25 DK DK231578A patent/DK155832C/da not_active IP Right Cessation
- 1978-05-25 NO NO781824A patent/NO146392C/no unknown
- 1978-05-25 LU LU79703A patent/LU79703A1/xx unknown
- 1978-05-25 IT IT49547/78A patent/IT1202822B/it active
- 1978-05-25 SE SE7806038A patent/SE448991B/sv not_active IP Right Cessation
- 1978-05-25 IE IE1047/78A patent/IE47072B1/en unknown
- 1978-05-26 BE BE188076A patent/BE867531A/xx not_active IP Right Cessation
- 1978-05-26 FR FR7815759A patent/FR2391998A1/fr active Granted
- 1978-05-26 CH CH578078A patent/CH644590A5/de not_active IP Right Cessation
- 1978-05-26 US US05/909,846 patent/US4181719A/en not_active Expired - Lifetime
-
1979
- 1979-04-02 US US06/026,329 patent/US4482495A/en not_active Expired - Lifetime
-
1981
- 1981-03-23 US US06/246,234 patent/US4361703A/en not_active Expired - Fee Related
-
1982
- 1982-03-22 US US06/360,312 patent/US4405800A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT7849547A0 (it) | 1978-05-25 |
| CH644590A5 (de) | 1984-08-15 |
| NL7805675A (nl) | 1978-11-28 |
| IE47072B1 (en) | 1983-12-14 |
| US4405800A (en) | 1983-09-20 |
| NL176070C (nl) | 1985-02-18 |
| BE867531A (fr) | 1978-09-18 |
| US4181719A (en) | 1980-01-01 |
| NL176070B (nl) | 1984-09-17 |
| NO146392C (no) | 1982-09-22 |
| DK155832C (da) | 1989-10-02 |
| DE2822789A1 (de) | 1978-12-07 |
| GB1583602A (en) | 1981-01-28 |
| LU79703A1 (fr) | 1978-11-06 |
| DE2822789C2 (de) | 1984-01-12 |
| DK231578A (da) | 1978-11-27 |
| IT1202822B (it) | 1989-02-09 |
| ATA380178A (de) | 1982-02-15 |
| NO781824L (no) | 1978-11-28 |
| FR2391998B1 (de) | 1981-11-13 |
| DK155832B (da) | 1989-05-22 |
| FR2391998A1 (fr) | 1978-12-22 |
| AT368489B (de) | 1982-10-11 |
| SE7806038L (sv) | 1978-11-27 |
| FI70208B (fi) | 1986-02-28 |
| US4361703A (en) | 1982-11-30 |
| US4482495A (en) | 1984-11-13 |
| NO146392B (no) | 1982-06-14 |
| IE781047L (en) | 1978-11-26 |
| FI781610A7 (fi) | 1978-11-27 |
| FI70208C (fi) | 1986-09-15 |
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Legal Events
| Date | Code | Title | Description |
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| NUG | Patent has lapsed |
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