CA1181419A - Amide derivatives of p-isobutyl-phenyl-propionic acid, process for their preparation and related pharmaceutical compositions - Google Patents
Amide derivatives of p-isobutyl-phenyl-propionic acid, process for their preparation and related pharmaceutical compositionsInfo
- Publication number
- CA1181419A CA1181419A CA000381957A CA381957A CA1181419A CA 1181419 A CA1181419 A CA 1181419A CA 000381957 A CA000381957 A CA 000381957A CA 381957 A CA381957 A CA 381957A CA 1181419 A CA1181419 A CA 1181419A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- isobutyl
- substituted amine
- propionic acid
- acid
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- -1 Amide derivatives of p-isobutyl-phenyl-propionic acid Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 6
- 235000003704 aspartic acid Nutrition 0.000 claims abstract description 6
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004472 Lysine Substances 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- REUQKCDCQVNKLW-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanamide Chemical compound CC(C)CC1=CC=C(C(C)C(N)=O)C=C1 REUQKCDCQVNKLW-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 239000004220 glutamic acid Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
- 230000002349 favourable effect Effects 0.000 abstract 1
- 229960001680 ibuprofen Drugs 0.000 description 19
- 241000700159 Rattus Species 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- 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 10
- 231100000419 toxicity Toxicity 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 102000002322 Egg Proteins Human genes 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 235000014103 egg white Nutrition 0.000 description 3
- 210000000969 egg white Anatomy 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 1
- HKXLAGBDJVHRQG-YFKPBYRVSA-N L-lysinamide Chemical compound NCCCC[C@H](N)C(N)=O HKXLAGBDJVHRQG-YFKPBYRVSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 238000001792 White test Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001618 algogenic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001779 embryotoxic effect Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 229940082151 ibuprofen 100 mg Drugs 0.000 description 1
- 229940082164 ibuprofen 50 mg Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000021332 multicellular organism growth Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23601/80A IT1193955B (it) | 1980-07-22 | 1980-07-22 | Derivati ammidici dell'acido p-isobutilfenilpropionico, procedimento per la loro preparazione e relative composizioni farmaceutici |
| IT23601A/80 | 1980-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1181419A true CA1181419A (en) | 1985-01-22 |
Family
ID=11208465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000381957A Expired CA1181419A (en) | 1980-07-22 | 1981-07-17 | Amide derivatives of p-isobutyl-phenyl-propionic acid, process for their preparation and related pharmaceutical compositions |
Country Status (16)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536346A (en) * | 1983-05-06 | 1985-08-20 | American Cyanamid Company | Aralkanamidophenyl compounds |
| HU198446B (en) * | 1987-09-25 | 1989-10-30 | Richter Gedeon Vegyeszet | Process for production of new amids of buten acid and medical compositions containing such active substances |
| IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| IT1318466B1 (it) * | 2000-04-14 | 2003-08-25 | Dompe Spa | Ammidi di acidi r-2-(amminoaril)-propionici, utili nella prevenzionedell'attivazione leucocitaria. |
| ITMI20010395A1 (it) | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
| EP1457485A1 (en) | 2003-03-14 | 2004-09-15 | Dompé S.P.A. | Sulfonic acids, their derivatives and pharmaceutical compositions containing them |
-
1980
- 1980-07-22 IT IT23601/80A patent/IT1193955B/it active
-
1981
- 1981-07-14 GB GB8121623A patent/GB2080797B/en not_active Expired
- 1981-07-17 CA CA000381957A patent/CA1181419A/en not_active Expired
- 1981-07-20 DE DE3128676A patent/DE3128676C2/de not_active Expired
- 1981-07-20 IN IN809/CAL/81A patent/IN153746B/en unknown
- 1981-07-20 LU LU83497A patent/LU83497A1/de unknown
- 1981-07-20 PT PT73400A patent/PT73400B/pt unknown
- 1981-07-21 JP JP56113098A patent/JPS5742663A/ja active Pending
- 1981-07-21 AR AR286159A patent/AR226734A1/es active
- 1981-07-21 MX MX819564U patent/MX7038E/es unknown
- 1981-07-21 ES ES504156A patent/ES504156A0/es active Granted
- 1981-07-21 KR KR1019810002639A patent/KR840001072B1/ko not_active Expired
- 1981-07-21 CH CH4755/81A patent/CH648292A5/it not_active IP Right Cessation
- 1981-07-22 BR BR8104728A patent/BR8104728A/pt unknown
- 1981-07-22 BE BE0/205465A patent/BE889699A/fr not_active IP Right Cessation
- 1981-07-22 FR FR8114252A patent/FR2491456B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8204414A1 (es) | 1982-05-16 |
| PT73400B (en) | 1982-10-01 |
| KR830006185A (ko) | 1983-09-20 |
| FR2491456B1 (enrdf_load_stackoverflow) | 1985-11-15 |
| GB2080797A (en) | 1982-02-10 |
| KR840001072B1 (ko) | 1984-07-31 |
| IN153746B (enrdf_load_stackoverflow) | 1984-08-18 |
| CH648292A5 (it) | 1985-03-15 |
| DE3128676A1 (de) | 1982-04-22 |
| ES504156A0 (es) | 1982-05-16 |
| IT8023601A0 (it) | 1980-07-22 |
| MX7038E (es) | 1987-03-18 |
| JPS5742663A (en) | 1982-03-10 |
| IT1193955B (it) | 1988-08-31 |
| LU83497A1 (de) | 1981-10-29 |
| AR226734A1 (es) | 1982-08-13 |
| BE889699A (fr) | 1981-11-16 |
| PT73400A (en) | 1981-08-01 |
| DE3128676C2 (de) | 1983-12-01 |
| GB2080797B (en) | 1984-01-18 |
| BR8104728A (pt) | 1982-04-13 |
| FR2491456A1 (enrdf_load_stackoverflow) | 1982-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |