CA1097659A - Derives n-acyl de la sydnonimine et methode de preparation - Google Patents
Derives n-acyl de la sydnonimine et methode de preparationInfo
- Publication number
- CA1097659A CA1097659A CA284,999A CA284999A CA1097659A CA 1097659 A CA1097659 A CA 1097659A CA 284999 A CA284999 A CA 284999A CA 1097659 A CA1097659 A CA 1097659A
- Authority
- CA
- Canada
- Prior art keywords
- phenylethyl
- beta
- methyl
- alpha
- sydnonimine
- 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
- 238000000034 method Methods 0.000 title claims description 39
- GSKDBLIBBOYOFU-UHFFFAOYSA-N oxadiazol-5-amine Chemical compound NC1=CN=NO1 GSKDBLIBBOYOFU-UHFFFAOYSA-N 0.000 title abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
- 230000010933 acylation Effects 0.000 claims description 9
- 238000005917 acylation reaction Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- -1 p-chlorophenylamino Chemical group 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical group ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 claims 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 34
- 230000000694 effects Effects 0.000 abstract description 11
- 239000003368 psychostimulant agent Substances 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- 230000003137 locomotive effect Effects 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- 206010042008 Stereotypy Diseases 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 208000000187 Abnormal Reflex Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000002269 analeptic agent Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 230000035859 hyperreflexia Effects 0.000 description 2
- 206010020745 hyperreflexia Diseases 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002582 psychostimulating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2423787 | 1976-11-25 | ||
| SU762423787A SU715575A1 (ru) | 1976-11-25 | 1976-11-25 | 3-( -Фенилизопропил)- фенилкарбамоилсиднонимин,обладающий психостимулирующей активностью |
| SU2425985 | 1976-11-30 | ||
| SU2425985 | 1978-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097659A true CA1097659A (fr) | 1981-03-17 |
Family
ID=26665602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,999A Expired CA1097659A (fr) | 1976-11-25 | 1977-08-18 | Derives n-acyl de la sydnonimine et methode de preparation |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5365880A (fr) |
| CA (1) | CA1097659A (fr) |
| DE (1) | DE2738022A1 (fr) |
| FR (1) | FR2372160A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2121785A4 (fr) * | 2007-03-14 | 2011-01-12 | Caliper Life Sciences Inc | Sydnonimines - inhibiteurs de réabsorption de dopamine spécifique et leur utilisation dans le traitement de troubles liés à la dopamine |
| US10188651B2 (en) | 2013-03-15 | 2019-01-29 | Melior Pharmaceuticals Ii, Llc | Methods of treating sleep disorders |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277609A (en) | 1979-08-31 | 1981-07-07 | American Home Products Corporation | Sydnone imines |
| US4324897A (en) * | 1980-10-02 | 1982-04-13 | American Home Products Corporation | 1,2,3 Oxadiazolium salts |
| US4289885A (en) | 1980-10-02 | 1981-09-15 | American Home Products Corporation | 3-[2-(Dimethylamino)-2-phenylethyl]N-[phenylamino)carbonyl]sydnone imine, a new central nervous system stimulant |
| US4301285A (en) | 1980-10-02 | 1981-11-17 | American Home Products Corporation | Sydnonimine CNS stimulants |
| US4371697A (en) | 1980-10-06 | 1983-02-01 | American Home Products Corporation | 3-[1-(Hydroxymethyl)-2-phenylethyl]-N-[(phenylamino)-carbonyl]sydnone imine |
| EP4282862A1 (fr) * | 2022-05-25 | 2023-11-29 | Irbm S.P.A. | Inhibiteurs de flavivirus |
-
1977
- 1977-08-18 CA CA284,999A patent/CA1097659A/fr not_active Expired
- 1977-08-23 DE DE19772738022 patent/DE2738022A1/de not_active Withdrawn
- 1977-08-26 FR FR7726079A patent/FR2372160A1/fr active Granted
- 1977-09-16 JP JP11063877A patent/JPS5365880A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2121785A4 (fr) * | 2007-03-14 | 2011-01-12 | Caliper Life Sciences Inc | Sydnonimines - inhibiteurs de réabsorption de dopamine spécifique et leur utilisation dans le traitement de troubles liés à la dopamine |
| US9604945B2 (en) | 2007-03-14 | 2017-03-28 | Caliper Life Sciences, Inc. | Sydnonimines-specific dopamine reuptake inhibitors and their use in treating dopamine related disorders |
| US10188651B2 (en) | 2013-03-15 | 2019-01-29 | Melior Pharmaceuticals Ii, Llc | Methods of treating sleep disorders |
| US11351169B2 (en) | 2013-03-15 | 2022-06-07 | Melior Pharmaceuticals Ii, Llc | Methods of treating dyskinesia and related disorders |
| US12048697B2 (en) | 2013-03-15 | 2024-07-30 | Melior Pharmaceuticals Ii, Llc | Methods of treating dyskinesia and related disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372160A1 (fr) | 1978-06-23 |
| FR2372160B1 (fr) | 1980-06-20 |
| DE2738022A1 (de) | 1978-06-01 |
| JPS5365880A (en) | 1978-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |