GB1560150A - 2 - (3' - substituted - 4' - (1'' - pyrryl)-phenyl) - propionic acids - Google Patents
2 - (3' - substituted - 4' - (1'' - pyrryl)-phenyl) - propionic acids Download PDFInfo
- Publication number
- GB1560150A GB1560150A GB49234/77A GB4923477A GB1560150A GB 1560150 A GB1560150 A GB 1560150A GB 49234/77 A GB49234/77 A GB 49234/77A GB 4923477 A GB4923477 A GB 4923477A GB 1560150 A GB1560150 A GB 1560150A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propionic acid
- acid
- propionamide
- nitro
- nitrophenyl
- 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
- 235000019260 propionic acid Nutrition 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000005599 propionic acid derivatives Chemical class 0.000 claims description 6
- NRXCEEGVEKQCBJ-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)propanamide Chemical compound NC(=O)C(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 NRXCEEGVEKQCBJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- GIZHRKQXPROIGC-UHFFFAOYSA-N 2-(4-chlorophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(Cl)C=C1 GIZHRKQXPROIGC-UHFFFAOYSA-N 0.000 claims description 4
- BKSYOYRLJJVUAN-UHFFFAOYSA-N 2-(4-amino-3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(N)C([N+]([O-])=O)=C1 BKSYOYRLJJVUAN-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 229910001963 alkali metal nitrate Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 2
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 229940080818 propionamide Drugs 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- PVCXBDATMRFUTO-UHFFFAOYSA-N 2-(4-amino-3-nitrophenyl)propanamide Chemical compound NC(=O)C(C)C1=CC=C(N)C([N+]([O-])=O)=C1 PVCXBDATMRFUTO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- VEQXXEKUBQWICL-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VEQXXEKUBQWICL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 1
- 101100533387 Homo sapiens SCGB1D1 gene Proteins 0.000 description 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 description 1
- 102100028659 Secretoglobin family 1D member 1 Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (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 |
|---|---|---|---|
| FR7635993A FR2371924A1 (fr) | 1976-11-30 | 1976-11-30 | Acides aryl-aliphatiques substitues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1560150A true GB1560150A (en) | 1980-01-30 |
Family
ID=9180445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49234/77A Expired GB1560150A (en) | 1976-11-30 | 1977-11-25 | 2 - (3' - substituted - 4' - (1'' - pyrryl)-phenyl) - propionic acids |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4190665A (enExample) |
| BE (1) | BE861043A (enExample) |
| CA (1) | CA1097663A (enExample) |
| CH (1) | CH626605A5 (enExample) |
| DE (1) | DE2751178C2 (enExample) |
| ES (1) | ES464182A1 (enExample) |
| FR (1) | FR2371924A1 (enExample) |
| GB (1) | GB1560150A (enExample) |
| NL (1) | NL7713253A (enExample) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH488695A (de) * | 1966-10-31 | 1970-04-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen, substituierten Phenylessigsäuren |
| CH500973A (de) * | 1966-10-31 | 1970-12-31 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Derivate von Phenylessigsäuren |
| NL170852C (nl) | 1968-03-27 | 1983-01-03 | Ciba Geigy Ag | Werkwijze ter bereiding van farmaceutische preparaten en werkwijze ter bereiding van anti-inflammatoir werkzaam p-isoindolinylfenylazijnzuur en van derivaten hiervan. |
| US3868391A (en) * | 1968-03-27 | 1975-02-25 | Ciba Geigy Corp | {60 -(cyclic tert, aminophenyl)-aliphatic acids |
| US3993763A (en) * | 1969-03-18 | 1976-11-23 | Ciba-Geigy Corporation | Tertiary aminoacids as anti-inflammatory agents |
| NL169735C (nl) | 1968-03-27 | 1982-08-16 | Ciba Geigy | Werkwijze ter bereiding of vervaardiging van anti-inflammatoir werkzame farmaceutische preparaten; alsmede werkwijze ter bereiding van anti-inflammatoir werkzame, op plaats 4 met een via stikstof gebonden, stikstof bevattende heterocyclische rest gesubstitueerde alfa-fenylpropionzuurderivaten. |
| GB1299172A (en) | 1968-10-15 | 1972-12-06 | Lilly Industries Ltd | Heterocyclic anti-inflammatory agents |
| CH504434A (de) * | 1969-06-23 | 1971-03-15 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Derivate von Phenylessigsäuren |
-
1976
- 1976-11-30 FR FR7635993A patent/FR2371924A1/fr active Granted
-
1977
- 1977-11-16 ES ES464182A patent/ES464182A1/es not_active Expired
- 1977-11-16 DE DE2751178A patent/DE2751178C2/de not_active Expired
- 1977-11-22 BE BE182801A patent/BE861043A/xx not_active IP Right Cessation
- 1977-11-22 CH CH1429177A patent/CH626605A5/fr not_active IP Right Cessation
- 1977-11-25 GB GB49234/77A patent/GB1560150A/en not_active Expired
- 1977-11-28 US US05/855,361 patent/US4190665A/en not_active Expired - Lifetime
- 1977-11-29 CA CA292,018A patent/CA1097663A/fr not_active Expired
- 1977-11-30 NL NL7713253A patent/NL7713253A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2751178C2 (de) | 1984-10-04 |
| ES464182A1 (es) | 1978-09-01 |
| CH626605A5 (enExample) | 1981-11-30 |
| DE2751178A1 (de) | 1978-06-01 |
| FR2371924B1 (enExample) | 1979-03-23 |
| BE861043A (fr) | 1978-05-22 |
| NL7713253A (nl) | 1978-06-01 |
| FR2371924A1 (fr) | 1978-06-23 |
| CA1097663A (fr) | 1981-03-17 |
| US4190665A (en) | 1980-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |