GB879259A - Acid addition salts of 2-dimethylaminoethanol and central nervous system stimulant compositions containing them - Google Patents
Acid addition salts of 2-dimethylaminoethanol and central nervous system stimulant compositions containing themInfo
- Publication number
- GB879259A GB879259A GB35979/57A GB3597957A GB879259A GB 879259 A GB879259 A GB 879259A GB 35979/57 A GB35979/57 A GB 35979/57A GB 3597957 A GB3597957 A GB 3597957A GB 879259 A GB879259 A GB 879259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- dimethylaminoethanol
- neutral
- salts
- addition salts
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title abstract 8
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical class CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 title abstract 7
- 150000003839 salts Chemical class 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 title abstract 2
- 239000002269 analeptic agent Chemical class 0.000 title 1
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 abstract 6
- 230000007935 neutral effect Effects 0.000 abstract 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 3
- 239000002156 adsorbate Substances 0.000 abstract 3
- 235000008160 pyridoxine Nutrition 0.000 abstract 3
- 239000011677 pyridoxine Substances 0.000 abstract 3
- 229940011671 vitamin b6 Drugs 0.000 abstract 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 abstract 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- -1 adenosinate Chemical compound 0.000 abstract 2
- 229940113720 aminosalicylate Drugs 0.000 abstract 2
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 abstract 2
- 239000002775 capsule Substances 0.000 abstract 2
- 239000003729 cation exchange resin Substances 0.000 abstract 2
- 229920001429 chelating resin Polymers 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 abstract 2
- 239000003937 drug carrier Substances 0.000 abstract 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract 2
- 239000007924 injection Substances 0.000 abstract 2
- 238000002347 injection Methods 0.000 abstract 2
- GHOKWGTUZJEAQD-UHFFFAOYSA-N pantothenic acid Chemical compound OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 abstract 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 2
- 229960001860 salicylate Drugs 0.000 abstract 2
- 239000008174 sterile solution Substances 0.000 abstract 2
- 229940095064 tartrate Drugs 0.000 abstract 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- VFYFMNCKPJDAPV-UHFFFAOYSA-N 2,2'-(5-oxo-1,3-dioxolan-4,4-diyl)diessigs Chemical compound C1N(C2)CN3CN1CN2C3.OC(=O)CC1(CC(O)=O)OCOC1=O VFYFMNCKPJDAPV-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 abstract 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019483 Peanut oil Nutrition 0.000 abstract 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 229940072107 ascorbate Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- ZZKLBPLJHJQUJL-UHFFFAOYSA-N benzoic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)C1=CC=CC=C1 ZZKLBPLJHJQUJL-UHFFFAOYSA-N 0.000 abstract 1
- 229940023913 cation exchange resins Drugs 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- CVSVTCORWBXHQV-UHFFFAOYSA-M creatinate Chemical compound NC(=N)N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-M 0.000 abstract 1
- 229960002104 cyanocobalamin Drugs 0.000 abstract 1
- 235000000639 cyanocobalamin Nutrition 0.000 abstract 1
- 239000011666 cyanocobalamin Substances 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 abstract 1
- 229940124280 l-arginine Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 239000011664 nicotinic acid Substances 0.000 abstract 1
- 239000000312 peanut oil Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 229960004799 tryptophan Drugs 0.000 abstract 1
Classifications
-
- 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
- C07D209/20—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 substituted additionally by nitrogen atoms, e.g. tryptophane
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- 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
-
- 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
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Adsorbates of 2-dimethylaminoethanol or cation-exchange resins include the adsorbates or "Dowex" 1-150 (a sulphonated copolymer of styrene and divinyl benzene) and "Amberlite" IRC-50 (a copolymer material having free carboxylic groups). ("Amberlite" and "Dowex" are Registered Trade Marks).ALSO:The invention comprises the lactate, acetate, ascorbate, nicotinate, neutral and acid citrates, neutral and acid tartarates, salicylate, adenosinate, creatinate, succinate, neutral and acid fumarates, phthalate, l-methionine, l-arginine, l-tryptophane, d-pantothenate, benzoate propionate, pyruvate, betaresorcylate, p-acetylaminobenzoate, 3,4,5,-trimethoxybenzoate ortho-aminosalicylate, meta-aminosalicylate and para-aminosalicylate salts of 2-dimethylaminoethanol, an adsorbate of 2-dimethylaminoethanol or a cation-exchange resin (see Group IV(a)) and pharmaceutical preparations containing salts of dimethylaminoethanol (see Group VI). The specific salts of the invention are prepared from the base and the appropriate acid.ALSO:Pharmaceutical compositions comprise either 2-dimethylamino ethanol or acid addition salts thereof and a pharmaceutical carrier in unit closage form or 2-dimethylamino ethanol acid addition salts other than the gallate or the p-aminobenzoate and a pharmaceutical carrier. The compositions may contain other active ingredients such as d-pantothenic acid, l-methionine, pyridoxine or cyanocobalamin. Examples are given of a tablet containing the acid tartrate, an elixir containing the betaresorcylate, an aqueous sterile solution for injection containing the neutral tartrate. A dry filled capsule containing the gallate, a capsule containing a solution of the salicylate in peanut oil, an aerosol preparation containing the base, a tablet containing the p-acetylamino benzoate together with pyridoxine, d-calcium pantothenate and l-methionine and a sterile solution for injection containing the hydrochloride salt, cyanocobaltamin, d-calcium pantathenate and pyridoxine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US879259XA | 1956-11-20 | 1956-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB879259A true GB879259A (en) | 1961-10-11 |
Family
ID=22208091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35979/57A Expired GB879259A (en) | 1956-11-20 | 1957-11-19 | Acid addition salts of 2-dimethylaminoethanol and central nervous system stimulant compositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB879259A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275643A (en) * | 1963-07-19 | 1966-09-27 | Irwin I Lubowe | Allantoin-pantothenate compounds |
| FR2068522A1 (en) * | 1969-08-28 | 1971-08-27 | Newport Pharmaceuticals | |
| FR2168245A1 (en) * | 1972-01-21 | 1973-08-31 | Eurap Sa | Dimethylamino ethanol pyridinecarboxylate - cholinergic and antiinflammatory |
| FR2295742A1 (en) * | 1974-12-24 | 1976-07-23 | Francaise Coop Pharma | N-methyl colamine pantothenate compsns - used to stimulate acetyl choline synthesis, e.g. to treat atropinic side effects of drugs |
| EP0217258A3 (en) * | 1985-09-28 | 1989-12-13 | Massachusetts Institute Of Technology | The use of choline or choline releasing compounds in the production of pharmacological compositions capable of reducing fatigue |
| FR2684297A1 (en) * | 1991-11-28 | 1993-06-04 | Bfb | USE OF SULFUR AMINO ACID FOR THE PREPARATION OF A MEDICINAL PRODUCT FOR THE TREATMENT OF ECZEMA. |
| US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
| WO1996012696A1 (en) * | 1994-10-20 | 1996-05-02 | Prospa B.V. | Salts of omega-3-polyunsaturated fatty acids and pharmaceutical formulations containing them |
| WO2005074946A1 (en) * | 2004-02-10 | 2005-08-18 | Adenobio N.V. | Stable and active complexes of adenosine and adenosine phosphates with aminoalcohols for the treatment of pulmonary artery hypertension, cardiac failure and other diseases |
| WO2008044099A1 (en) * | 2006-10-09 | 2008-04-17 | Carlo Ghisalberti | Charge transfer complexes in the treatment of inflammatory bowel diseases |
| CN102344379A (en) * | 2004-04-07 | 2012-02-08 | 约克大学 | Ionic liquids containing nitrogen-containing cations |
| US8168789B2 (en) | 2007-09-27 | 2012-05-01 | Toyama Chemical Co., Ltd. | Organic amine salt of 6-fluoro-3-hydroxy-2-pyrazinecarbonitrile and method for producing the same |
| CN108658793A (en) * | 2018-06-25 | 2018-10-16 | 安徽大学 | Synthesis process of di (dimethylaminoethyl) phthalate |
-
1957
- 1957-11-19 GB GB35979/57A patent/GB879259A/en not_active Expired
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275643A (en) * | 1963-07-19 | 1966-09-27 | Irwin I Lubowe | Allantoin-pantothenate compounds |
| FR2068522A1 (en) * | 1969-08-28 | 1971-08-27 | Newport Pharmaceuticals | |
| FR2168245A1 (en) * | 1972-01-21 | 1973-08-31 | Eurap Sa | Dimethylamino ethanol pyridinecarboxylate - cholinergic and antiinflammatory |
| FR2295742A1 (en) * | 1974-12-24 | 1976-07-23 | Francaise Coop Pharma | N-methyl colamine pantothenate compsns - used to stimulate acetyl choline synthesis, e.g. to treat atropinic side effects of drugs |
| EP0217258A3 (en) * | 1985-09-28 | 1989-12-13 | Massachusetts Institute Of Technology | The use of choline or choline releasing compounds in the production of pharmacological compositions capable of reducing fatigue |
| FR2684297A1 (en) * | 1991-11-28 | 1993-06-04 | Bfb | USE OF SULFUR AMINO ACID FOR THE PREPARATION OF A MEDICINAL PRODUCT FOR THE TREATMENT OF ECZEMA. |
| EP0545759A1 (en) * | 1991-11-28 | 1993-06-09 | Société BFB | Use of a sulfur containing amino acid, eventually in combination with pyridoxine, for the preparation of a medicament for the treatment of eczema |
| US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
| WO1996012696A1 (en) * | 1994-10-20 | 1996-05-02 | Prospa B.V. | Salts of omega-3-polyunsaturated fatty acids and pharmaceutical formulations containing them |
| WO2005074946A1 (en) * | 2004-02-10 | 2005-08-18 | Adenobio N.V. | Stable and active complexes of adenosine and adenosine phosphates with aminoalcohols for the treatment of pulmonary artery hypertension, cardiac failure and other diseases |
| US7585850B2 (en) | 2004-02-10 | 2009-09-08 | Adenobio N.V. | Stable and active complexes of adenosine and adenosine phosphates with aminoalcohols for the treatment of pulmonary artery hypertension, cardiac failure and other diseases |
| CN102344379A (en) * | 2004-04-07 | 2012-02-08 | 约克大学 | Ionic liquids containing nitrogen-containing cations |
| US8784686B2 (en) | 2004-04-07 | 2014-07-22 | Innovia Films Limited | Liquids |
| US8992798B2 (en) | 2004-04-07 | 2015-03-31 | Innovia Films Limited | Liquids |
| US9328220B2 (en) | 2004-04-07 | 2016-05-03 | Innovia Films Limited | Liquids |
| WO2008044099A1 (en) * | 2006-10-09 | 2008-04-17 | Carlo Ghisalberti | Charge transfer complexes in the treatment of inflammatory bowel diseases |
| US8168789B2 (en) | 2007-09-27 | 2012-05-01 | Toyama Chemical Co., Ltd. | Organic amine salt of 6-fluoro-3-hydroxy-2-pyrazinecarbonitrile and method for producing the same |
| CN108658793A (en) * | 2018-06-25 | 2018-10-16 | 安徽大学 | Synthesis process of di (dimethylaminoethyl) phthalate |
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