SE453917B - Derivat av glycinamid samt framstellning derav och farmaceutisk komposition innehallande denna - Google Patents
Derivat av glycinamid samt framstellning derav och farmaceutisk komposition innehallande dennaInfo
- Publication number
- SE453917B SE453917B SE8002204A SE8002204A SE453917B SE 453917 B SE453917 B SE 453917B SE 8002204 A SE8002204 A SE 8002204A SE 8002204 A SE8002204 A SE 8002204A SE 453917 B SE453917 B SE 453917B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- branched
- formula
- linear
- straight
- Prior art date
Links
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 31
- -1 alkenyl radical Chemical class 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- GJNNXIYZWIZFRH-UHFFFAOYSA-N 2-(pentylamino)acetamide Chemical compound CCCCCNCC(N)=O GJNNXIYZWIZFRH-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- QEJUSMMBSMNFBF-UHFFFAOYSA-N 2-(hexylamino)acetamide Chemical compound CCCCCCNCC(N)=O QEJUSMMBSMNFBF-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000004036 acetal group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- BKCWSIQDMQGRQU-UHFFFAOYSA-N 2-(octylamino)acetamide Chemical compound CCCCCCCCNCC(N)=O BKCWSIQDMQGRQU-UHFFFAOYSA-N 0.000 claims description 4
- CEMZQHFVTGKVFJ-UHFFFAOYSA-N 2-(pentylamino)butanamide Chemical compound CCCCCNC(CC)C(N)=O CEMZQHFVTGKVFJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- FDTRJHZIKLUURP-UHFFFAOYSA-N 2-(decylamino)acetamide Chemical compound CCCCCCCCCCNCC(N)=O FDTRJHZIKLUURP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- QILHEBHCIWDHRY-UHFFFAOYSA-N 2-(oct-7-en-2-ylamino)acetamide Chemical compound NC(=O)CNC(C)CCCCC=C QILHEBHCIWDHRY-UHFFFAOYSA-N 0.000 claims description 2
- 241000167854 Bourreria succulenta Species 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 235000019693 cherries Nutrition 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
- 229940093471 ethyl oleate Drugs 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 239000008223 sterile water Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 240000002470 Amphicarpaea bracteata Species 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 230000009467 reduction Effects 0.000 description 18
- 150000002825 nitriles Chemical class 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 241000699670 Mus sp. Species 0.000 description 13
- 238000006460 hydrolysis reaction Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 10
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 9
- 230000009471 action Effects 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000013256 coordination polymer 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 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 150000001409 amidines Chemical group 0.000 description 7
- 230000036461 convulsion Effects 0.000 description 7
- DNSCECUSJKDSKP-UHFFFAOYSA-N hydron;2-(pentylamino)acetamide;chloride Chemical compound Cl.CCCCCNCC(N)=O DNSCECUSJKDSKP-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU81069A LU81069A1 (fr) | 1979-03-22 | 1979-03-22 | Derive de glycinamide, preparation de ce derive, son utilisation ainsi que composition contenant ce derive |
| LU81068A LU81068A1 (fr) | 1979-03-22 | 1979-03-22 | Derives de la glycinamide, leur preparation et utilisation, ainsi que compositions contenant ces derives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8002204L SE8002204L (sv) | 1980-09-23 |
| SE453917B true SE453917B (sv) | 1988-03-14 |
Family
ID=26640253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8002204A SE453917B (sv) | 1979-03-22 | 1980-03-21 | Derivat av glycinamid samt framstellning derav och farmaceutisk komposition innehallande denna |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4639468A (enExample) |
| AT (1) | AT381302B (enExample) |
| AU (1) | AU536499B2 (enExample) |
| CA (1) | CA1184567A (enExample) |
| CH (1) | CH645091A5 (enExample) |
| DE (2) | DE3050800C2 (enExample) |
| DK (1) | DK162714C (enExample) |
| ES (1) | ES490536A0 (enExample) |
| FI (1) | FI82033C (enExample) |
| FR (1) | FR2451913A1 (enExample) |
| GB (1) | GB2048852B (enExample) |
| GR (1) | GR68005B (enExample) |
| IE (1) | IE49751B1 (enExample) |
| IL (1) | IL59679A (enExample) |
| NL (1) | NL191508C (enExample) |
| NO (1) | NO157817C (enExample) |
| PT (1) | PT70992A (enExample) |
| SE (1) | SE453917B (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937698A1 (de) * | 1979-09-18 | 1981-04-02 | A. Nattermann & Cie GmbH, 5000 Köln | N-propionylsarcosinanilide, deren herstellungsverfahren und arzneimittel auf deren basis |
| DK373383A (da) * | 1982-08-20 | 1984-02-21 | Midit | Fremgangsmaade til fremstilling af omega-aminosyrederivater |
| US4798687A (en) * | 1987-02-06 | 1989-01-17 | Pennwalt Corporation | 2-Amino-N-[1,2-Diphenyl-1-(thifluoromethyl)ethyl]acetamide derivatives |
| US4904681A (en) * | 1987-12-01 | 1990-02-27 | G. D. Searle & Co. | D-cycloserine and its prodrugs as cognitive enhancers |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| US5278191A (en) * | 1988-08-31 | 1994-01-11 | G. D. Searle & Co. | Diphenylmethylaminoacetamide derivatives as anti-convulsants |
| US5288905A (en) * | 1988-10-07 | 1994-02-22 | G. D. Searle & Co. | Glycyl urea derivatives as anti-convulsants |
| US4944796A (en) * | 1988-11-14 | 1990-07-31 | Ici Americas Inc. | Certain 2-(disubstituted amino) acetanilide herbicides |
| DE3915755A1 (de) * | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
| IL94466A (en) * | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
| US5075337A (en) * | 1989-07-26 | 1991-12-24 | G. D. Searle & Co. | Alpha-deuterated 2-alkylaminoacetamide derivatives having reduced toxicity for treatment of CNS disorders |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| DE4102042A1 (de) * | 1991-01-24 | 1992-07-30 | Bayer Ag | Substituierte aminosaeureamid-derivate deren herstellung und verwendung als fungizide |
| US5141960A (en) * | 1991-06-25 | 1992-08-25 | G. D. Searle & Co. | Tricyclic glycinamide derivatives as anti-convulsants |
| GB9306899D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylalkylaminobenzyl) aminopropionamide derivatives and process for their preparation |
| GB9306886D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylakoxybenzyl) aminopropanamide derivatives and process for their preparation |
| US5585358A (en) * | 1993-07-06 | 1996-12-17 | Yissum Research Development Corporation Of The Hebrew University Of Jerusalem | Derivatives of valproic acid amides and 2-valproenoic acid amides, method of making and use thereof as anticonvulsant agents |
| US6191165B1 (en) * | 1996-05-31 | 2001-02-20 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| CA2254833C (en) * | 1996-05-31 | 2008-04-29 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| IT1283489B1 (it) * | 1996-07-23 | 1998-04-21 | Chiesi Farma Spa | Ammidi di alfa-amminoacidi,loro preparazione e loro impiego terapeutico |
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| DE69937340T2 (de) * | 1998-03-26 | 2008-07-17 | University Of Saskatchewan, Saskatoon | Aliphatische aminosäure und aminophosphonsäure, aminonitrile und aminotetrazole als zellulares rettungsmittel |
| US6984754B1 (en) | 1998-03-26 | 2006-01-10 | University Of Saskatchewan Technologies Inc. | Aliphatic amino carboxylic and amino phosphonic acids amino nitriles and amino tetrazoles as cellular rescue agents |
| US6346547B1 (en) * | 1999-02-08 | 2002-02-12 | Checkpoint, Genetics, Inc. | N-substituted amino acids, antioxidant pharmaceutical compositions containing n-substituted amino acids and methods for preventing cardiovascular diseases and/or preventing and/or treating antioxidant responsive diseases therewith |
| AU2001280699A1 (en) * | 2000-07-21 | 2002-02-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Use of derivatives of valproic acid and 2-valproenic acid amides for the treatment of mania in bipolar disorder |
| SI1311256T1 (sl) * | 2000-08-17 | 2005-12-31 | Teva Pharma | Uporaba derivatov amidov valprojske kisline in amidov 2-valproenske kisline za zdravljenje ali preprecevanje bolecin in/ali glavobolnih motenj |
| EP1339669B1 (en) * | 2000-11-21 | 2008-06-04 | UCB Pharma, S.A. | N-alkylated gaba compounds, processes for their preparation and their use as medicaments |
| CN1219776C (zh) | 2001-02-16 | 2005-09-21 | 阿雷里克斯神经学有限公司 | 作为glyt－1抑制剂的噻吩取代的胺衍生物 |
| US20030035784A1 (en) * | 2001-03-05 | 2003-02-20 | Kao Corporation | Hair cosmetic, aminocarboxylic acid amide and method for producing the same |
| EP1423168B1 (en) | 2001-09-03 | 2006-02-08 | Newron Pharmaceuticals S.p.A. | Pharmaceutical composition comprising gabapentin or an analogue thereof and an alpha-aminoamide and its analgesic use |
| EP1438956A1 (en) * | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
| DE602005021907D1 (de) * | 2004-09-10 | 2010-07-29 | Newron Pharm Spa | Verwendung von (r)-(halogenbenzyloxy)-benzylamino-propanamiden als natrium- und/oder calciumkanal-selektive modulatoren |
| CN101018843B (zh) * | 2004-09-13 | 2011-05-11 | 西巴特殊化学品控股有限公司 | 烷基氨基乙酰胺润滑添加剂 |
| FR2896991A1 (fr) * | 2006-02-03 | 2007-08-10 | Inst Nat Sante Rech Med | Procede pour preparer un compose organique a l'etat solide et compositions pharmaceutiques comprenant ledit compose organique |
| CN102351733B (zh) * | 2011-07-21 | 2014-03-19 | 凯莱英医药化学（阜新）技术有限公司 | 一种制备2-氨基-n,n-二甲基乙酰胺盐酸盐的方法 |
| EP3766916B1 (en) | 2014-06-25 | 2022-09-28 | Acuitas Therapeutics Inc. | Novel lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| JP6053724B2 (ja) * | 2014-06-26 | 2016-12-27 | 国立大学法人九州大学 | イオン交換樹脂及び金属の吸着分離方法 |
| HRP20240865T1 (hr) | 2015-06-29 | 2024-10-11 | Acuitas Therapeutics Inc. | Lipidi i formulacije lipidnih nanočestica za isporuku nukleinskih kiselina |
| CN113636947A (zh) | 2015-10-28 | 2021-11-12 | 爱康泰生治疗公司 | 用于递送核酸的新型脂质和脂质纳米颗粒制剂 |
| CN106187829B (zh) * | 2016-07-29 | 2017-12-15 | 万华化学集团股份有限公司 | 一种制备乙二胺基乙磺酸盐的方法 |
| US12491261B2 (en) | 2016-10-26 | 2025-12-09 | Acuitas Therapeutics, Inc. | Lipid nanoparticle formulations |
| US11357856B2 (en) | 2017-04-13 | 2022-06-14 | Acuitas Therapeutics, Inc. | Lipids for delivery of active agents |
| IL301115A (en) | 2017-04-28 | 2023-05-01 | Acuitas Therapeutics Inc | Novel carbonyl lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| CA3073020A1 (en) | 2017-08-16 | 2019-02-21 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| US11524932B2 (en) | 2017-08-17 | 2022-12-13 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| WO2019036028A1 (en) | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | LIPIDS FOR USE IN LIPID NANOPARTICULAR FORMULATIONS |
| CA3073018A1 (en) | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| IL322436A (en) | 2018-09-21 | 2025-09-01 | Acuitas Therapeutics Inc | Systems and methods for producing lipid nanoparticles and liposomes |
| KR101953366B1 (ko) | 2018-12-26 | 2019-02-28 | 정종문 | 침향을 포함하는 기억력 및 인지능력을 향상시키는 기능성 건강식품 및 이의 제조방법 |
| CN113474328B (zh) | 2019-01-11 | 2025-07-11 | 爱康泰生治疗公司 | 用于脂质纳米颗粒递送活性剂的脂质 |
| USD926577S1 (en) | 2019-09-23 | 2021-08-03 | Verdant Ventures | Tamper-resistant lid assembly |
| US11326923B2 (en) | 2019-10-08 | 2022-05-10 | Verdant Ventures | Tamper-resistant lid assembly for dispensing a premeasured amount of liquid |
| AU2021308681A1 (en) | 2020-07-16 | 2023-03-09 | Acuitas Therapeutics, Inc. | Cationic lipids for use in lipid nanoparticles |
| CN118647600A (zh) | 2021-12-16 | 2024-09-13 | 爱康泰生治疗公司 | 用于脂质纳米颗粒制剂的脂质 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2368208A (en) * | 1940-12-16 | 1945-01-30 | Emulsol Corp | Chemical compounds and method of preparing same |
| US2781385A (en) * | 1953-09-21 | 1957-02-12 | Gefgy Chemical Corp | Diamidocarboxylic acids and certain salts thereof |
| LU43649A1 (enExample) * | 1962-05-09 | 1963-07-16 | ||
| JPS5319654B2 (enExample) | 1974-03-14 | 1978-06-22 | ||
| DE2832009A1 (de) | 1978-07-20 | 1980-01-31 | Deutsches Krebsforsch | Verwendung von sarkosin und sarkosinderivaten ls tumorhemmende wirksubstanzen |
-
1980
- 1980-03-20 DE DE3050800A patent/DE3050800C2/de not_active Expired
- 1980-03-20 DE DE19803010599 patent/DE3010599A1/de active Granted
- 1980-03-21 CH CH225380A patent/CH645091A5/fr not_active IP Right Cessation
- 1980-03-21 SE SE8002204A patent/SE453917B/sv not_active IP Right Cessation
- 1980-03-21 NO NO800830A patent/NO157817C/no unknown
- 1980-03-21 ES ES490536A patent/ES490536A0/es active Granted
- 1980-03-21 DK DK123580A patent/DK162714C/da not_active IP Right Cessation
- 1980-03-21 FR FR8006390A patent/FR2451913A1/fr active Granted
- 1980-03-21 FI FI800900A patent/FI82033C/fi not_active IP Right Cessation
- 1980-03-21 IL IL59679A patent/IL59679A/xx unknown
- 1980-03-21 AT AT0154680A patent/AT381302B/de not_active IP Right Cessation
- 1980-03-21 PT PT70992A patent/PT70992A/pt active IP Right Revival
- 1980-03-22 GR GR61512A patent/GR68005B/el unknown
- 1980-03-24 IE IE599/80A patent/IE49751B1/en not_active IP Right Cessation
- 1980-03-24 CA CA000348319A patent/CA1184567A/en not_active Expired
- 1980-03-24 NL NL8001721A patent/NL191508C/xx not_active IP Right Cessation
- 1980-03-24 AU AU56784/80A patent/AU536499B2/en not_active Expired
- 1980-03-24 GB GB8009801A patent/GB2048852B/en not_active Expired
-
1985
- 1985-08-23 US US06/768,185 patent/US4639468A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK123580A (da) | 1980-09-23 |
| IE800599L (en) | 1980-09-22 |
| PT70992A (fr) | 1980-04-01 |
| AU536499B2 (en) | 1984-05-10 |
| IL59679A (en) | 1984-11-30 |
| IE49751B1 (en) | 1985-12-11 |
| CH645091A5 (fr) | 1984-09-14 |
| FI800900A7 (fi) | 1980-09-23 |
| DK162714C (da) | 1992-04-21 |
| ES8104790A1 (es) | 1981-04-16 |
| GR68005B (enExample) | 1981-10-26 |
| IL59679A0 (en) | 1980-06-30 |
| GB2048852B (en) | 1983-03-30 |
| FR2451913B1 (enExample) | 1984-07-13 |
| NO157817B (no) | 1988-02-15 |
| GB2048852A (en) | 1980-12-17 |
| SE8002204L (sv) | 1980-09-23 |
| NO800830L (no) | 1980-09-23 |
| AU5678480A (en) | 1980-09-25 |
| FI82033C (fi) | 1991-01-10 |
| DK162714B (da) | 1991-12-02 |
| ES490536A0 (es) | 1981-04-16 |
| NL191508B (nl) | 1995-04-18 |
| CA1184567A (en) | 1985-03-26 |
| DE3050800C2 (enExample) | 1989-06-22 |
| AT381302B (de) | 1986-09-25 |
| DE3010599A1 (de) | 1980-10-09 |
| NO157817C (no) | 1988-05-25 |
| NL8001721A (nl) | 1980-09-24 |
| FR2451913A1 (fr) | 1980-10-17 |
| FI82033B (fi) | 1990-09-28 |
| NL191508C (nl) | 1995-08-21 |
| ATA154680A (de) | 1986-02-15 |
| DE3010599C2 (enExample) | 1989-03-02 |
| US4639468A (en) | 1987-01-27 |
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