DE1618849B1 - Phenylisopropylamidverbindungen und Verfahren zu ihrer Herstellung - Google Patents
Phenylisopropylamidverbindungen und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1618849B1 DE1618849B1 DE1967S0108220 DES0108220A DE1618849B1 DE 1618849 B1 DE1618849 B1 DE 1618849B1 DE 1967S0108220 DE1967S0108220 DE 1967S0108220 DE S0108220 A DES0108220 A DE S0108220A DE 1618849 B1 DE1618849 B1 DE 1618849B1
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethylphenyl
- isopropyl
- parts
- isopropylamine
- acid chloride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical class CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 m-Trifluoromethylphenyl Chemical group 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 6
- 239000003208 petroleum Substances 0.000 claims 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 4
- 229940080818 propionamide Drugs 0.000 claims 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 claims 1
- DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical compound OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 claims 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims 1
- DOZZSWAOPDYVLH-UHFFFAOYSA-N 2-phenylpropanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1 DOZZSWAOPDYVLH-UHFFFAOYSA-N 0.000 claims 1
- FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-UHFFFAOYSA-N 0.000 claims 1
- BDUBTLFQHNYXPC-UHFFFAOYSA-N 3-methylbut-2-enoyl chloride Chemical compound CC(C)=CC(Cl)=O BDUBTLFQHNYXPC-UHFFFAOYSA-N 0.000 claims 1
- BZPHJDQWFRMGER-UHFFFAOYSA-N 3-phenylprop-2-ynoyl chloride Chemical compound ClC(=O)C#CC1=CC=CC=C1 BZPHJDQWFRMGER-UHFFFAOYSA-N 0.000 claims 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims 1
- 239000001856 Ethyl cellulose Substances 0.000 claims 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
- 229920000084 Gum arabic Polymers 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
- 241000978776 Senegalia senegal Species 0.000 claims 1
- 239000000205 acacia gum Substances 0.000 claims 1
- 235000010489 acacia gum Nutrition 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
- 235000019325 ethyl cellulose Nutrition 0.000 claims 1
- 229920001249 ethyl cellulose Polymers 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 1
- 229960000581 salicylamide Drugs 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 235000012222 talc Nutrition 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002830 appetite depressant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 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
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical compound CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000011102 Thera Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000678 effect on lipid Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000005830 nonesterified fatty acids Chemical class 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10815/66A GB1150051A (en) | 1966-03-11 | 1966-03-11 | New Phenylisopropylamide Derivatives and Process for Preparing Them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618849B1 true DE1618849B1 (de) | 1971-12-23 |
Family
ID=9974801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967S0108220 Pending DE1618849B1 (de) | 1966-03-11 | 1967-02-08 | Phenylisopropylamidverbindungen und Verfahren zu ihrer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3504028A (cg-RX-API-DMAC7.html) |
| BE (1) | BE694932A (cg-RX-API-DMAC7.html) |
| CH (1) | CH471084A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1618849B1 (cg-RX-API-DMAC7.html) |
| FR (2) | FR1570423A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1150051A (cg-RX-API-DMAC7.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2029385A1 (cg-RX-API-DMAC7.html) * | 1969-01-27 | 1970-10-23 | Science Union & Cie | |
| US3950335A (en) * | 1970-05-02 | 1976-04-13 | Boehringer Ingelheim Gmbh | 1-(3'-trifluoromethyl-4'-chloro-phenyl)-2-amino-propanes and salts thereof |
| US4053509A (en) * | 1971-11-15 | 1977-10-11 | Schering Corporation | Substituted aryl and aralkyl amides |
| US3944675A (en) * | 1973-03-15 | 1976-03-16 | Schering Corporation | Substituted aryl and aralkyl amides in the treatment of parkinsonism |
| US4532139A (en) * | 1983-07-14 | 1985-07-30 | The Procter & Gamble Company | Compounds and compositions useful for producing analgesia |
| ZA853997B (en) * | 1984-05-28 | 1986-01-29 | Ciba Geigy Ag | Composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides |
| AU2003225277A1 (en) * | 2002-05-02 | 2003-11-17 | Robert Harris | Lipid removal from the body |
| DE102005062985A1 (de) * | 2005-12-28 | 2007-07-05 | Grünenthal GmbH | Substituierte bis(hetero)aromatische N-Ethylpropiolamide und ihre Verwendung zur Herstellung von Arzneimitteln |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL270984A (cg-RX-API-DMAC7.html) * | 1960-11-05 | |||
| US3244718A (en) * | 1964-02-17 | 1966-04-05 | Biel John Hans | Piperazine derivatives |
-
1966
- 1966-03-11 GB GB10815/66A patent/GB1150051A/en not_active Expired
-
1967
- 1967-02-08 DE DE1967S0108220 patent/DE1618849B1/de active Pending
- 1967-02-27 US US619006A patent/US3504028A/en not_active Expired - Lifetime
- 1967-03-02 BE BE694932D patent/BE694932A/xx unknown
- 1967-03-09 FR FR1570423D patent/FR1570423A/fr not_active Expired
- 1967-03-10 CH CH353967A patent/CH471084A/fr not_active IP Right Cessation
- 1967-06-08 FR FR109622A patent/FR6507M/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1150051A (en) | 1969-04-30 |
| FR1570423A (cg-RX-API-DMAC7.html) | 1969-06-13 |
| BE694932A (cg-RX-API-DMAC7.html) | 1967-09-04 |
| FR6507M (cg-RX-API-DMAC7.html) | 1968-12-02 |
| CH471084A (fr) | 1969-04-15 |
| US3504028A (en) | 1970-03-31 |
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