CA1043800A - HYDROXAMIC ACID DERIVATIVES OF SUBSTITUTED .alpha.-AMINOOXYCARBOXYLIC ACIDS AND A PROCESS FOR THE PREPARATION THEREOF - Google Patents
HYDROXAMIC ACID DERIVATIVES OF SUBSTITUTED .alpha.-AMINOOXYCARBOXYLIC ACIDS AND A PROCESS FOR THE PREPARATION THEREOFInfo
- Publication number
- CA1043800A CA1043800A CA214,945A CA214945A CA1043800A CA 1043800 A CA1043800 A CA 1043800A CA 214945 A CA214945 A CA 214945A CA 1043800 A CA1043800 A CA 1043800A
- Authority
- CA
- Canada
- Prior art keywords
- group
- general formula
- hydroxylamine
- process according
- chlorobenzyl
- 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 claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 30
- 150000007513 acids Chemical class 0.000 title description 5
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- -1 dinitro- phenyl Chemical group 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 239000002262 Schiff base Substances 0.000 claims abstract description 7
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 7
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000006277 halobenzyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 16
- 229940086542 triethylamine Drugs 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 2
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims description 2
- MVWOCMNWNNVFHI-UHFFFAOYSA-N 2-(cyclopentylideneamino)oxyacetic acid Chemical compound OC(=O)CON=C1CCCC1 MVWOCMNWNNVFHI-UHFFFAOYSA-N 0.000 claims 1
- 241000965481 Darksidea alpha Species 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- GONDHKVGJCQJPR-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=C(Cl)C=C1 GONDHKVGJCQJPR-UHFFFAOYSA-N 0.000 claims 1
- VIFDVZZLHVXUHV-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl]hydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=C(Cl)C=C1 VIFDVZZLHVXUHV-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000001549 tubercolostatic effect Effects 0.000 abstract description 2
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 abstract 1
- 201000008827 tuberculosis Diseases 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000186363 Mycobacterium kansasii Species 0.000 description 1
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 1
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- JTXJZBMXQMTSQN-UHFFFAOYSA-N amino hydrogen carbonate Chemical class NOC(O)=O JTXJZBMXQMTSQN-UHFFFAOYSA-N 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VNUUSOJDAJMVLQ-UHFFFAOYSA-N ethyl 2-aminooxyacetate Chemical compound CCOC(=O)CON VNUUSOJDAJMVLQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 125000006480 iodobenzyl group Chemical group 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000528 HU167363B (cs) | 1973-11-29 | 1973-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043800A true CA1043800A (en) | 1978-12-05 |
Family
ID=11000939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA214,945A Expired CA1043800A (en) | 1973-11-29 | 1974-11-29 | HYDROXAMIC ACID DERIVATIVES OF SUBSTITUTED .alpha.-AMINOOXYCARBOXYLIC ACIDS AND A PROCESS FOR THE PREPARATION THEREOF |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5337338B2 (cs) |
| AT (1) | AT338776B (cs) |
| BE (1) | BE822765A (cs) |
| CA (1) | CA1043800A (cs) |
| CH (2) | CH603576A5 (cs) |
| CS (2) | CS177050B2 (cs) |
| DD (1) | DD118863A5 (cs) |
| DE (1) | DE2455432A1 (cs) |
| FR (1) | FR2252844B1 (cs) |
| GB (1) | GB1446833A (cs) |
| HU (1) | HU167363B (cs) |
| NL (1) | NL7415518A (cs) |
| SU (2) | SU558639A3 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE52765T1 (de) * | 1984-10-18 | 1990-06-15 | Shell Int Research | Alpha-aminooxy-c4-alkansaeuren und -ester. |
| JP2839888B2 (ja) * | 1987-08-19 | 1998-12-16 | 三菱製紙株式会社 | ノーカーボン感圧複写紙 |
| US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
-
1973
- 1973-11-29 HU HURI000528 patent/HU167363B/hu unknown
-
1974
- 1974-11-21 CH CH1549374A patent/CH603576A5/xx not_active IP Right Cessation
- 1974-11-21 CH CH1065177A patent/CH605705A5/xx not_active IP Right Cessation
- 1974-11-22 GB GB5068974A patent/GB1446833A/en not_active Expired
- 1974-11-22 DE DE19742455432 patent/DE2455432A1/de active Pending
- 1974-11-25 AT AT940374A patent/AT338776B/de not_active IP Right Cessation
- 1974-11-26 CS CS862775A patent/CS177050B2/cs unknown
- 1974-11-26 CS CS808874A patent/CS177039B2/cs unknown
- 1974-11-27 DD DD18261074A patent/DD118863A5/xx unknown
- 1974-11-28 NL NL7415518A patent/NL7415518A/xx not_active Application Discontinuation
- 1974-11-28 SU SU2082858A patent/SU558639A3/ru active
- 1974-11-29 CA CA214,945A patent/CA1043800A/en not_active Expired
- 1974-11-29 FR FR7439307A patent/FR2252844B1/fr not_active Expired
- 1974-11-29 BE BE150995A patent/BE822765A/xx unknown
- 1974-11-29 JP JP13638374A patent/JPS5337338B2/ja not_active Expired
-
1976
- 1976-05-28 SU SU762364205A patent/SU593660A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CH603576A5 (cs) | 1978-08-31 |
| FR2252844B1 (cs) | 1979-09-21 |
| BE822765A (fr) | 1975-03-14 |
| JPS5084541A (cs) | 1975-07-08 |
| FR2252844A1 (cs) | 1975-06-27 |
| HU167363B (cs) | 1975-09-27 |
| JPS5337338B2 (cs) | 1978-10-07 |
| SU593660A3 (ru) | 1978-02-15 |
| CS177050B2 (cs) | 1977-07-29 |
| CS177039B2 (cs) | 1977-07-29 |
| DD118863A5 (cs) | 1976-03-20 |
| SU558639A3 (ru) | 1977-05-15 |
| GB1446833A (en) | 1976-08-18 |
| AT338776B (de) | 1977-09-12 |
| DE2455432A1 (de) | 1975-06-05 |
| CH605705A5 (cs) | 1978-10-13 |
| ATA940374A (de) | 1977-01-15 |
| NL7415518A (nl) | 1975-06-02 |
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