NO861917L - Analogifremgangsmaate for fremstilling av farmakologisk aktive propionylanilider. - Google Patents
Analogifremgangsmaate for fremstilling av farmakologisk aktive propionylanilider.Info
- Publication number
- NO861917L NO861917L NO861917A NO861917A NO861917L NO 861917 L NO861917 L NO 861917L NO 861917 A NO861917 A NO 861917A NO 861917 A NO861917 A NO 861917A NO 861917 L NO861917 L NO 861917L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- propionylanilides
- reaction
- acid
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 14
- -1 4-isobutylphenyl Chemical group 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 230000002969 morbid Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 230000000954 anitussive effect Effects 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 230000001754 anti-pyretic effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 206010011224 Cough Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 244000144993 groups of animals Species 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IZCCWISLNJGJIZ-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IZCCWISLNJGJIZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000037114 Symptom Flare Up Diseases 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pulmonology (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)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20726/85A IT1191617B (it) | 1985-05-15 | 1985-05-15 | Propionilanilidi farmacologicamente attive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO861917L true NO861917L (no) | 1986-11-17 |
Family
ID=11171140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO861917A NO861917L (no) | 1985-05-15 | 1986-05-14 | Analogifremgangsmaate for fremstilling av farmakologisk aktive propionylanilider. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4639449A (de) |
| EP (1) | EP0202482B1 (de) |
| JP (1) | JPS61263966A (de) |
| AT (1) | ATE56445T1 (de) |
| CA (1) | CA1260470A (de) |
| DE (1) | DE3674060D1 (de) |
| DK (1) | DK222886A (de) |
| ES (1) | ES8706653A1 (de) |
| IT (1) | IT1191617B (de) |
| NO (1) | NO861917L (de) |
| PT (1) | PT82535B (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1518375A1 (de) * | 1965-06-08 | 1969-08-14 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen 2-Amino-halogenbenzylaminen |
| US3769408A (en) * | 1965-06-08 | 1973-10-30 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing a halo-substituted 2-amino-benzylamine-morpholide or a salt thereof |
-
1985
- 1985-05-15 IT IT20726/85A patent/IT1191617B/it active
-
1986
- 1986-04-18 AT AT86105409T patent/ATE56445T1/de not_active IP Right Cessation
- 1986-04-18 DE DE8686105409T patent/DE3674060D1/de not_active Expired - Fee Related
- 1986-04-18 EP EP86105409A patent/EP0202482B1/de not_active Expired - Lifetime
- 1986-04-23 US US06/854,789 patent/US4639449A/en not_active Expired - Fee Related
- 1986-05-05 CA CA000508348A patent/CA1260470A/en not_active Expired
- 1986-05-07 PT PT82535A patent/PT82535B/pt unknown
- 1986-05-13 JP JP61107804A patent/JPS61263966A/ja active Pending
- 1986-05-14 ES ES554933A patent/ES8706653A1/es not_active Expired
- 1986-05-14 NO NO861917A patent/NO861917L/no unknown
- 1986-05-14 DK DK222886A patent/DK222886A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK222886D0 (da) | 1986-05-14 |
| IT1191617B (it) | 1988-03-23 |
| PT82535A (en) | 1986-06-01 |
| DK222886A (da) | 1986-11-16 |
| JPS61263966A (ja) | 1986-11-21 |
| DE3674060D1 (de) | 1990-10-18 |
| ES8706653A1 (es) | 1987-07-01 |
| US4639449A (en) | 1987-01-27 |
| PT82535B (en) | 1987-09-23 |
| EP0202482A1 (de) | 1986-11-26 |
| ES554933A0 (es) | 1987-07-01 |
| EP0202482B1 (de) | 1990-09-12 |
| ATE56445T1 (de) | 1990-09-15 |
| CA1260470A (en) | 1989-09-26 |
| IT8520726A0 (it) | 1985-05-15 |
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