CA1292015C - 1-¬N-(.alpha.-AMINO-.alpha.-METHYLACETYL)AMINOPHENYL|-2-AMINOPROPANONE DERIVATIVES - Google Patents
1-¬N-(.alpha.-AMINO-.alpha.-METHYLACETYL)AMINOPHENYL|-2-AMINOPROPANONE DERIVATIVESInfo
- Publication number
- CA1292015C CA1292015C CA000488854A CA488854A CA1292015C CA 1292015 C CA1292015 C CA 1292015C CA 000488854 A CA000488854 A CA 000488854A CA 488854 A CA488854 A CA 488854A CA 1292015 C CA1292015 C CA 1292015C
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- crl
- methylacetyl
- aminophenyl
- amino
- 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 - Lifetime
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000001430 anti-depressive effect Effects 0.000 abstract description 4
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 239000000021 stimulant Substances 0.000 abstract 1
- 241000699670 Mus sp. Species 0.000 description 20
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 5
- 229960004046 apomorphine Drugs 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 206010021143 Hypoxia Diseases 0.000 description 4
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229960002319 barbital Drugs 0.000 description 4
- 230000006399 behavior Effects 0.000 description 4
- 230000002631 hypothermal effect Effects 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- 206010002660 Anoxia Diseases 0.000 description 3
- 241000976983 Anoxia Species 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 3
- 206010042008 Stereotypy Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 230000007953 anoxia Effects 0.000 description 3
- 239000007928 intraperitoneal injection Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 3
- 229960003147 reserpine Drugs 0.000 description 3
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000037023 motor activity Effects 0.000 description 2
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- REEUVFCVXKWOFE-UHFFFAOYSA-K gallamine triethiodide Chemical compound [I-].[I-].[I-].CC[N+](CC)(CC)CCOC1=CC=CC(OCC[N+](CC)(CC)CC)=C1OCC[N+](CC)(CC)CC REEUVFCVXKWOFE-UHFFFAOYSA-K 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- -1 methylacetyl Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000842 neuromuscular blocking agent Substances 0.000 description 1
- 231100001160 nonlethal Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (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 |
|---|---|---|---|
| FR8412964A FR2569186B1 (fr) | 1984-08-20 | 1984-08-20 | Derives de 1-(n-(a-amino-a-methylacetyl)-aminophenyl)-2-amino-propanone, procede de preparation et utilisation en therapeutique |
| FR8412964 | 1984-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1292015C true CA1292015C (en) | 1991-11-12 |
Family
ID=9307108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000488854A Expired - Lifetime CA1292015C (en) | 1984-08-20 | 1985-08-16 | 1-¬N-(.alpha.-AMINO-.alpha.-METHYLACETYL)AMINOPHENYL|-2-AMINOPROPANONE DERIVATIVES |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4690950A (en, 2012) |
| EP (1) | EP0174887B1 (en, 2012) |
| JP (1) | JPS6165855A (en, 2012) |
| AT (1) | ATE28071T1 (en, 2012) |
| AU (1) | AU570820B2 (en, 2012) |
| CA (1) | CA1292015C (en, 2012) |
| DE (1) | DE3560291D1 (en, 2012) |
| DK (1) | DK378885A (en, 2012) |
| ES (1) | ES8605472A1 (en, 2012) |
| FR (1) | FR2569186B1 (en, 2012) |
| GR (1) | GR851996B (en, 2012) |
| PT (1) | PT80992B (en, 2012) |
| ZA (1) | ZA856150B (en, 2012) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2128255A (en) * | 1934-12-22 | 1938-08-30 | Gen Aniline Works Inc | Azo dyestuffs |
| DE1015986B (de) * | 1955-07-04 | 1957-09-19 | Thomae Gmbh Dr K | Licht- und Sonnenschutzmittel |
| FR1463813A (fr) * | 1964-02-26 | 1966-07-22 | Ciba Geigy | Nouvelles amino-phénylcétones et procédé pour leur préparation |
| NL7308131A (en, 2012) * | 1971-12-13 | 1974-12-16 | ||
| US4024282A (en) * | 1975-11-25 | 1977-05-17 | Mitsubishi Chemical Industries Ltd. | Pharmaceutically active 2-(3-alkylaminopropoxy)diphenylmethanes |
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
| GB1531781A (en) * | 1976-03-23 | 1978-11-08 | Lafon Labor | N-propargyl-piperonylamine and its preparation and use |
| CA1086733A (en) * | 1976-12-06 | 1980-09-30 | Ryoji Kikumoto | Pharmaceutically active 2-substituted-1-(omega- aminoalkoxy) benzenes |
| US4650771A (en) * | 1983-11-04 | 1987-03-17 | Miles Laboratories, Inc. | Immunogens, antibodies, labeled conjugates, and related derivatives for lidocaine and analogs thereof |
| ATE62222T1 (de) * | 1985-02-15 | 1991-04-15 | Res Corp Technologies Inc | Aminosaeure-derivate und ihre anwendung zur herstellung eines antikrampfmittels. |
-
1984
- 1984-08-20 FR FR8412964A patent/FR2569186B1/fr not_active Expired
-
1985
- 1985-08-07 DE DE8585401609T patent/DE3560291D1/de not_active Expired
- 1985-08-07 AT AT85401609T patent/ATE28071T1/de not_active IP Right Cessation
- 1985-08-07 EP EP85401609A patent/EP0174887B1/fr not_active Expired
- 1985-08-14 ZA ZA856150A patent/ZA856150B/xx unknown
- 1985-08-16 CA CA000488854A patent/CA1292015C/en not_active Expired - Lifetime
- 1985-08-16 GR GR851996A patent/GR851996B/el unknown
- 1985-08-16 US US06/766,636 patent/US4690950A/en not_active Expired - Fee Related
- 1985-08-16 ES ES546859A patent/ES8605472A1/es not_active Expired
- 1985-08-20 AU AU46464/85A patent/AU570820B2/en not_active Ceased
- 1985-08-20 DK DK378885A patent/DK378885A/da unknown
- 1985-08-20 PT PT80992A patent/PT80992B/pt not_active IP Right Cessation
- 1985-08-20 JP JP60183804A patent/JPS6165855A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATE28071T1 (de) | 1987-07-15 |
| US4690950A (en) | 1987-09-01 |
| GR851996B (en, 2012) | 1985-12-17 |
| AU570820B2 (en) | 1988-03-24 |
| JPS6165855A (ja) | 1986-04-04 |
| ZA856150B (en) | 1986-04-30 |
| EP0174887B1 (fr) | 1987-07-01 |
| PT80992A (fr) | 1985-09-01 |
| AU4646485A (en) | 1986-02-27 |
| FR2569186A1 (fr) | 1986-02-21 |
| FR2569186B1 (fr) | 1986-09-05 |
| EP0174887A1 (fr) | 1986-03-19 |
| DK378885A (da) | 1986-02-21 |
| PT80992B (pt) | 1987-09-30 |
| ES546859A0 (es) | 1986-03-16 |
| DE3560291D1 (en) | 1987-08-06 |
| DK378885D0 (da) | 1985-08-20 |
| ES8605472A1 (es) | 1986-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |