ES366545A1 - Substituted phenylalkanoic acids - Google Patents
Substituted phenylalkanoic acidsInfo
- Publication number
- ES366545A1 ES366545A1 ES366545A ES366545A ES366545A1 ES 366545 A1 ES366545 A1 ES 366545A1 ES 366545 A ES366545 A ES 366545A ES 366545 A ES366545 A ES 366545A ES 366545 A1 ES366545 A1 ES 366545A1
- Authority
- ES
- Spain
- Prior art keywords
- pyrryl
- rch
- r1ch
- compounds
- 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
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- -1 1 - pyrryl Chemical group 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
- KLKFUQVAHJKMCI-UHFFFAOYSA-N 3-(4-aminophenyl)-2-methyl-3-oxopropanoic acid Chemical compound NC1=CC=C(C(=O)C(C(=O)O)C)C=C1 KLKFUQVAHJKMCI-UHFFFAOYSA-N 0.000 abstract 2
- CRAJBXINXVPCPE-UHFFFAOYSA-N 4-(4-acetamido-3-chlorophenyl)butanoic acid Chemical compound N(C(=O)C)C1=C(C=C(C=C1)CCCC(=O)O)Cl CRAJBXINXVPCPE-UHFFFAOYSA-N 0.000 abstract 1
- YDUDSQOJLRADBS-UHFFFAOYSA-N 4-oxo-4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound N1(C=CC=C1)C1=CC=C(C(=O)CCC(=O)O)C=C1 YDUDSQOJLRADBS-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Abstract
The invention comprises compounds of formula wherein Z is CH 2 or CO and R 1 is H, F or Cl, and their pharmaceutically acceptable salts. These compounds may be prepared by (1) reacting succinaldehyde or its derivative with a p-aminophenylbutyric or p-aminobenzoylpropionic acid (2) decarboxylating the corresponding malonic acid (3) hydrolysing the corresponding nitrile, alkyl ester or imido-ether (4) reacting an alkyl 2 - acetyl - 4 - [p - (1 - pyrryl) phenyl] butyrate with alkali metal hydroxide (for Z = CH 2 ) (5) reducing the compound where Z = CO to that where Z = CH 2 . Details are given for the preparation of the following starting materials and intermediates: 4 - (4 - acetamino - 3 - chlorophenyl) butyric acid ethyl 3-(p-aminophenyl) propionate RCO 2 Et, RCH 2 OH, RCH 2 Cl, RCH 2 OTs-(p), RCH(CO 2 Et) 2 and BCH(CO 2 H) 2 [where R = p - (1 - pyrryl) phenethyl] and R1CH(CO 2 Et) 2 , R1CH(CO 2 H) 2 and R1CH 2 CO 2 Et [where R1= 3 - chloro - 4 - (1 - pyrryl) phenethyl]. Also prepared is the 2,4-dinitrophenylhydrazone of 3-[p-(1-pyrryl) benzoyl] propionic acid. Therapeutic compositions for oral, rectal, local or parenteral administration comprise compounds of the above general formula, which have analgesic, antiphlogistic and antipyretic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH637968A CH500189A (en) | 1968-04-29 | 1968-04-29 | Process for the preparation of new, substituted phenylalkanoic acids |
| CH1732968A CH507234A (en) | 1968-04-29 | 1968-11-20 | Process for the production of new, substituted alkanoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES366545A1 true ES366545A1 (en) | 1971-01-01 |
Family
ID=25699490
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES366545A Expired ES366545A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
| ES366547A Expired ES366547A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
| ES366546A Expired ES366546A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
| ES366544A Expired ES366544A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES366547A Expired ES366547A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
| ES366546A Expired ES366546A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
| ES366544A Expired ES366544A1 (en) | 1968-04-29 | 1969-04-28 | Substituted phenylalkanoic acids |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3651084A (en) |
| JP (2) | JPS4813550B1 (en) |
| AT (5) | AT290518B (en) |
| BE (1) | BE732301A (en) |
| BG (5) | BG15547A3 (en) |
| CH (2) | CH500189A (en) |
| CS (4) | CS161852B2 (en) |
| DE (1) | DE1921651A1 (en) |
| DK (1) | DK125132C (en) |
| ES (4) | ES366545A1 (en) |
| FI (1) | FI50971C (en) |
| FR (1) | FR2007555A1 (en) |
| GB (1) | GB1264367A (en) |
| IE (1) | IE33116B1 (en) |
| IL (1) | IL32089A (en) |
| NL (1) | NL6906209A (en) |
| NO (1) | NO129572B (en) |
| PL (1) | PL69906B1 (en) |
| SE (1) | SE338994B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183276A (en) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | double-sided adhesive tape |
| JPS6183275A (en) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | Manufacturing method for double-sided adhesive tape |
| FI74723C (en) * | 1986-10-24 | 1988-03-10 | Yhtyneet Paperitehtaat Oy | HAEFTPRODUKT. |
-
1968
- 1968-04-29 CH CH637968A patent/CH500189A/en not_active IP Right Cessation
- 1968-11-20 CH CH1732968A patent/CH507234A/en not_active IP Right Cessation
-
1969
- 1969-04-22 NO NO691670A patent/NO129572B/no unknown
- 1969-04-22 FI FI691195A patent/FI50971C/en active
- 1969-04-22 NL NL6906209A patent/NL6906209A/xx unknown
- 1969-04-22 DK DK219769AA patent/DK125132C/en active
- 1969-04-22 US US818393A patent/US3651084A/en not_active Expired - Lifetime
- 1969-04-22 SE SE05684/69A patent/SE338994B/xx unknown
- 1969-04-28 GB GB2152369A patent/GB1264367A/en not_active Expired
- 1969-04-28 IE IE577/69A patent/IE33116B1/en unknown
- 1969-04-28 CS CS7997*A patent/CS161852B2/cs unknown
- 1969-04-28 CS CS7999*A patent/CS161854B2/cs unknown
- 1969-04-28 CS CS7998*A patent/CS161853B2/cs unknown
- 1969-04-28 ES ES366545A patent/ES366545A1/en not_active Expired
- 1969-04-28 ES ES366547A patent/ES366547A1/en not_active Expired
- 1969-04-28 BG BG013039A patent/BG15547A3/en unknown
- 1969-04-28 IL IL6932089A patent/IL32089A/en unknown
- 1969-04-28 AT AT189170A patent/AT290518B/en not_active IP Right Cessation
- 1969-04-28 DE DE19691921651 patent/DE1921651A1/en active Pending
- 1969-04-28 AT AT189270A patent/AT290519B/en not_active IP Right Cessation
- 1969-04-28 AT AT409069A patent/AT286976B/en active
- 1969-04-28 ES ES366546A patent/ES366546A1/en not_active Expired
- 1969-04-28 AT AT189070A patent/AT290517B/en not_active IP Right Cessation
- 1969-04-28 CS CS3005A patent/CS161851B2/cs unknown
- 1969-04-28 ES ES366544A patent/ES366544A1/en not_active Expired
- 1969-04-28 PL PL1969133260A patent/PL69906B1/pl unknown
- 1969-04-28 BG BG012132A patent/BG15206A3/en unknown
- 1969-04-28 AT AT189370A patent/AT290520B/en not_active IP Right Cessation
- 1969-04-29 BE BE732301D patent/BE732301A/xx unknown
- 1969-04-29 FR FR6913602A patent/FR2007555A1/fr not_active Withdrawn
- 1969-09-17 BG BG013040A patent/BG15548A3/en unknown
- 1969-09-17 BG BG013037A patent/BG15752A3/en unknown
- 1969-09-17 BG BG013038A patent/BG15546A3/en unknown
-
1971
- 1971-10-22 JP JP46083858A patent/JPS4813550B1/ja active Pending
- 1971-10-22 JP JP46083856A patent/JPS4827309B1/ja active Pending
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