CH497898A - Verfahren zur Herstellung wässriger Lösungen von praktisch wasserunlöslichen Phenoxyessigsäureamiden - Google Patents
Verfahren zur Herstellung wässriger Lösungen von praktisch wasserunlöslichen PhenoxyessigsäureamidenInfo
- Publication number
- CH497898A CH497898A CH1146062A CH1146062A CH497898A CH 497898 A CH497898 A CH 497898A CH 1146062 A CH1146062 A CH 1146062A CH 1146062 A CH1146062 A CH 1146062A CH 497898 A CH497898 A CH 497898A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- methoxy
- water
- phenoxyacetic acid
- fatty
- Prior art date
Links
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title claims description 10
- 239000002904 solvent Substances 0.000 title abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000013543 active substance Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 abstract description 8
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 abstract description 7
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 abstract description 7
- -1 fatty acid esters Chemical class 0.000 abstract description 6
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 239000004081 narcotic agent Substances 0.000 abstract description 4
- 210000003462 vein Anatomy 0.000 abstract description 4
- 238000001990 intravenous administration Methods 0.000 abstract description 3
- 238000010253 intravenous injection Methods 0.000 abstract description 3
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 3
- 229920000151 polyglycol Polymers 0.000 abstract description 3
- 239000010695 polyglycol Substances 0.000 abstract description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 abstract description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000004665 fatty acids Chemical class 0.000 abstract description 2
- 150000002191 fatty alcohols Chemical class 0.000 abstract description 2
- 239000010685 fatty oil Substances 0.000 abstract description 2
- 235000000346 sugar Nutrition 0.000 abstract description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 abstract 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 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 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 235000013681 dietary sucrose Nutrition 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 230000007794 irritation Effects 0.000 abstract 1
- 239000002736 nonionic surfactant Substances 0.000 abstract 1
- 239000001593 sorbitan monooleate Substances 0.000 abstract 1
- 229940035049 sorbitan monooleate Drugs 0.000 abstract 1
- 235000011069 sorbitan monooleate Nutrition 0.000 abstract 1
- 229960004793 sucrose Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- AXNKGLDCLYLVLQ-UHFFFAOYSA-N acetamidoeugenol Chemical compound CCN(CC)C(=O)COC1=CC=C(CC=C)C=C1OC AXNKGLDCLYLVLQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- FQBPCNCFOCPCJP-UHFFFAOYSA-N 2-(2-methoxy-4-prop-2-enylphenoxy)acetic acid Chemical compound COC1=CC(CC=C)=CC=C1OCC(O)=O FQBPCNCFOCPCJP-UHFFFAOYSA-N 0.000 description 2
- KGUHOFWIXKIURA-VQXBOQCVSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dodecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCC)O[C@@H]1O[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](CO)O1 KGUHOFWIXKIURA-VQXBOQCVSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940032085 sucrose monolaurate Drugs 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- DPPINZDLUUCYKL-UHFFFAOYSA-N 2-(4-acetyl-2-ethoxyphenoxy)-N,N-diethylacetamide Chemical compound C(C)N(C(COC1=C(C=C(C=C1)C(C)=O)OCC)=O)CC DPPINZDLUUCYKL-UHFFFAOYSA-N 0.000 description 1
- VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 210000002565 arteriole Anatomy 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NUQDJSMHGCTKNL-UHFFFAOYSA-N cyclohexyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1CCCCC1 NUQDJSMHGCTKNL-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical group CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- RPBKGXGYDGXYGA-UHFFFAOYSA-N n,n-diethyl-2-(2-methoxy-4-prop-1-enylphenoxy)acetamide Chemical compound CCN(CC)C(=O)COC1=CC=C(C=CC)C=C1OC RPBKGXGYDGXYGA-UHFFFAOYSA-N 0.000 description 1
- BOORGPJEETYENA-UHFFFAOYSA-N n,n-diethyl-2-(2-methoxy-4-propylphenoxy)acetamide Chemical compound CCCC1=CC=C(OCC(=O)N(CC)CC)C(OC)=C1 BOORGPJEETYENA-UHFFFAOYSA-N 0.000 description 1
- DYUSVPKMWAMYDH-UHFFFAOYSA-N n-ethoxyethanamine Chemical compound CCNOCC DYUSVPKMWAMYDH-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- KEJXLQUPYHWCNM-UHFFFAOYSA-N propanidid Chemical compound CCCOC(=O)CC1=CC=C(OCC(=O)N(CC)CC)C(OC)=C1 KEJXLQUPYHWCNM-UHFFFAOYSA-N 0.000 description 1
- 229960004948 propanidid Drugs 0.000 description 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- ZBCAZEFVTIBZJS-UHFFFAOYSA-M sodium;2-benzamidoacetate Chemical compound [Na+].[O-]C(=O)CNC(=O)C1=CC=CC=C1 ZBCAZEFVTIBZJS-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
- B65B61/00—Auxiliary devices, not otherwise provided for, for operating on sheets, blanks, webs, binding material, containers or packages
- B65B61/02—Auxiliary devices, not otherwise provided for, for operating on sheets, blanks, webs, binding material, containers or packages for perforating, scoring, slitting, or applying code or date marks on material prior to packaging
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Mechanical Engineering (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35258A DE1182388B (de) | 1961-10-31 | 1961-10-31 | Verfahren zur Herstellung von sterilisierbaren waessrigen Loesungen von narkotisch wirkenden Phenoxyessigsaeureamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH497898A true CH497898A (de) | 1970-10-31 |
Family
ID=7095928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1146062A CH497898A (de) | 1961-10-31 | 1962-09-28 | Verfahren zur Herstellung wässriger Lösungen von praktisch wasserunlöslichen Phenoxyessigsäureamiden |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE624258A (en)van) |
| BR (1) | BR6243886D0 (en)van) |
| CH (1) | CH497898A (en)van) |
| DE (1) | DE1182388B (en)van) |
| GB (1) | GB941694A (en)van) |
| NL (2) | NL145144B (en)van) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR880100602A (el) * | 1987-09-15 | 1989-06-22 | Sandoz Ag | Υδατοδιαλυτοι μονοεστερες ως διαλυτοποιητες για φαρμακολογικως δραστικες ενωσεις και φαρμακευτικα εκδοχα |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2474262C (en) | 2002-01-25 | 2011-03-15 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| WO2005009420A2 (en) * | 2003-07-23 | 2005-02-03 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
| US9421199B2 (en) | 2014-06-24 | 2016-08-23 | Sydnexis, Inc. | Ophthalmic composition |
| WO2016172712A2 (en) | 2015-04-23 | 2016-10-27 | Sydnexis, Inc. | Ophthalmic composition |
| US11382909B2 (en) | 2014-09-05 | 2022-07-12 | Sydnexis, Inc. | Ophthalmic composition |
| WO2016196367A1 (en) | 2015-05-29 | 2016-12-08 | Sydnexis, Inc. | D2o stabilized pharmaceutical formulations |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1091288B (de) * | 1958-07-03 | 1960-10-20 | Geigy Ag J R | Verfahren zur Herstellung injizierbarer Loesungen von Narkoticis |
| DE1089510B (de) * | 1959-03-23 | 1960-09-22 | Rudolf Reiss Dr | Verfahren zur Herstellung waessriger, injizierbarer Loesungen von 2-Methoxy-4-allylphenoxyessigsaeure-N, N-Diaethylamid |
-
0
- NL NL284933D patent/NL284933A/xx unknown
- BE BE624258D patent/BE624258A/xx unknown
-
1961
- 1961-10-31 DE DEF35258A patent/DE1182388B/de active Pending
-
1962
- 1962-09-28 CH CH1146062A patent/CH497898A/de not_active IP Right Cessation
- 1962-10-09 GB GB3820662A patent/GB941694A/en not_active Expired
- 1962-10-17 BR BR14388662A patent/BR6243886D0/pt unknown
- 1962-10-31 NL NL284933A patent/NL145144B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR880100602A (el) * | 1987-09-15 | 1989-06-22 | Sandoz Ag | Υδατοδιαλυτοι μονοεστερες ως διαλυτοποιητες για φαρμακολογικως δραστικες ενωσεις και φαρμακευτικα εκδοχα |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6243886D0 (pt) | 1973-05-29 |
| GB941694A (en) | 1963-11-13 |
| BE624258A (en)van) | |
| NL284933A (en)van) | |
| DE1182388B (de) | 1964-11-26 |
| NL145144B (nl) | 1975-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |