FI82033C - Foerfarande foer framstaellning av terapeutiskt aktivt glycinamidderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktivt glycinamidderivat. Download PDFInfo
- Publication number
- FI82033C FI82033C FI800900A FI800900A FI82033C FI 82033 C FI82033 C FI 82033C FI 800900 A FI800900 A FI 800900A FI 800900 A FI800900 A FI 800900A FI 82033 C FI82033 C FI 82033C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- formula
- reaction
- amine
- temperature
- Prior art date
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- 238000000034 method Methods 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000001408 amides Chemical group 0.000 claims description 20
- 150000002825 nitriles Chemical class 0.000 claims description 19
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- GJNNXIYZWIZFRH-UHFFFAOYSA-N 2-(pentylamino)acetamide Chemical compound CCCCCNCC(N)=O GJNNXIYZWIZFRH-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000004185 ester group Chemical group 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 70
- 238000006243 chemical reaction Methods 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
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- 239000000243 solution Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- -1 cycloaliphatic Chemical group 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 230000000694 effects Effects 0.000 description 20
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- 238000003786 synthesis reaction Methods 0.000 description 18
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- 241000699670 Mus sp. Species 0.000 description 14
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 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
- 239000007787 solid Substances 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 9
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- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
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- 238000001816 cooling Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 150000001409 amidines Chemical group 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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- 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
- 230000002378 acidificating effect Effects 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 150000004820 halides Chemical group 0.000 description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- 150000002527 isonitriles Chemical class 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
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- VQCBKKUSNRKMDB-UHFFFAOYSA-N oxiran-2-imine Chemical compound N=C1CO1 VQCBKKUSNRKMDB-UHFFFAOYSA-N 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 3
- QEJUSMMBSMNFBF-UHFFFAOYSA-N 2-(hexylamino)acetamide Chemical compound CCCCCCNCC(N)=O QEJUSMMBSMNFBF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- 229960002036 phenytoin Drugs 0.000 description 1
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 102000014898 transaminase activity proteins Human genes 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU81068 | 1979-03-22 | ||
| LU81069A LU81069A1 (fr) | 1979-03-22 | 1979-03-22 | Derive de glycinamide, preparation de ce derive, son utilisation ainsi que composition contenant ce derive |
| LU81069 | 1979-03-22 | ||
| LU81068A LU81068A1 (fr) | 1979-03-22 | 1979-03-22 | Derives de la glycinamide, leur preparation et utilisation, ainsi que compositions contenant ces derives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI800900A7 FI800900A7 (fi) | 1980-09-23 |
| FI82033B FI82033B (fi) | 1990-09-28 |
| FI82033C true FI82033C (fi) | 1991-01-10 |
Family
ID=26640253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI800900A FI82033C (fi) | 1979-03-22 | 1980-03-21 | Foerfarande foer framstaellning av terapeutiskt aktivt glycinamidderivat. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4639468A (online.php) |
| AT (1) | AT381302B (online.php) |
| AU (1) | AU536499B2 (online.php) |
| CA (1) | CA1184567A (online.php) |
| CH (1) | CH645091A5 (online.php) |
| DE (2) | DE3010599A1 (online.php) |
| DK (1) | DK162714C (online.php) |
| ES (1) | ES8104790A1 (online.php) |
| FI (1) | FI82033C (online.php) |
| FR (1) | FR2451913A1 (online.php) |
| GB (1) | GB2048852B (online.php) |
| GR (1) | GR68005B (online.php) |
| IE (1) | IE49751B1 (online.php) |
| IL (1) | IL59679A (online.php) |
| NL (1) | NL191508C (online.php) |
| NO (1) | NO157817C (online.php) |
| PT (1) | PT70992A (online.php) |
| SE (1) | SE453917B (online.php) |
Families Citing this family (55)
| 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 |
| FI832935A7 (fi) * | 1982-08-20 | 1984-02-21 | Midit | Derivat av w-aminosyror, deras framstaellning samt dessa derivat innehaollande blandningar |
| 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 |
| GB9306886D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylakoxybenzyl) aminopropanamide derivatives and process for their preparation |
| GB9306899D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylalkylaminobenzyl) aminopropionamide 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 |
| CZ294348B6 (cs) * | 1996-05-31 | 2004-12-15 | Allelix Neuroscience Inc. | Substituovaný derivát glycinu a farmaceutický prostředek s jeho obsahem |
| 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 |
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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 (online.php) * | 1962-05-09 | 1963-07-16 | ||
| JPS5319654B2 (online.php) | 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 DE19803010599 patent/DE3010599A1/de active Granted
- 1980-03-20 DE DE3050800A patent/DE3050800C2/de not_active Expired
- 1980-03-21 FR FR8006390A patent/FR2451913A1/fr active Granted
- 1980-03-21 PT PT70992A patent/PT70992A/pt active IP Right Revival
- 1980-03-21 FI FI800900A patent/FI82033C/fi not_active IP Right Cessation
- 1980-03-21 NO NO800830A patent/NO157817C/no unknown
- 1980-03-21 DK DK123580A patent/DK162714C/da not_active IP Right Cessation
- 1980-03-21 SE SE8002204A patent/SE453917B/sv 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 ES ES490536A patent/ES8104790A1/es not_active Expired
- 1980-03-21 CH CH225380A patent/CH645091A5/fr not_active IP Right Cessation
- 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 NL NL8001721A patent/NL191508C/xx not_active IP Right Cessation
- 1980-03-24 CA CA000348319A patent/CA1184567A/en not_active Expired
- 1980-03-24 GB GB8009801A patent/GB2048852B/en not_active Expired
- 1980-03-24 AU AU56784/80A patent/AU536499B2/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 |
|---|---|
| GR68005B (online.php) | 1981-10-26 |
| ES490536A0 (es) | 1981-04-16 |
| DE3010599A1 (de) | 1980-10-09 |
| NO800830L (no) | 1980-09-23 |
| NL8001721A (nl) | 1980-09-24 |
| DK162714B (da) | 1991-12-02 |
| NO157817C (no) | 1988-05-25 |
| DE3050800C2 (online.php) | 1989-06-22 |
| SE8002204L (sv) | 1980-09-23 |
| GB2048852A (en) | 1980-12-17 |
| GB2048852B (en) | 1983-03-30 |
| DK162714C (da) | 1992-04-21 |
| FI800900A7 (fi) | 1980-09-23 |
| PT70992A (fr) | 1980-04-01 |
| IL59679A (en) | 1984-11-30 |
| FI82033B (fi) | 1990-09-28 |
| NL191508C (nl) | 1995-08-21 |
| CA1184567A (en) | 1985-03-26 |
| FR2451913A1 (fr) | 1980-10-17 |
| AU536499B2 (en) | 1984-05-10 |
| ATA154680A (de) | 1986-02-15 |
| AU5678480A (en) | 1980-09-25 |
| SE453917B (sv) | 1988-03-14 |
| FR2451913B1 (online.php) | 1984-07-13 |
| NO157817B (no) | 1988-02-15 |
| US4639468A (en) | 1987-01-27 |
| IE49751B1 (en) | 1985-12-11 |
| NL191508B (nl) | 1995-04-18 |
| ES8104790A1 (es) | 1981-04-16 |
| DE3010599C2 (online.php) | 1989-03-02 |
| IE800599L (en) | 1980-09-22 |
| IL59679A0 (en) | 1980-06-30 |
| AT381302B (de) | 1986-09-25 |
| CH645091A5 (fr) | 1984-09-14 |
| DK123580A (da) | 1980-09-23 |
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