IE33116L - Pyrryl-phenyl alkanoic acids - Google Patents
Pyrryl-phenyl alkanoic acidsInfo
- Publication number
- IE33116L IE33116L IE690577A IE57769A IE33116L IE 33116 L IE33116 L IE 33116L IE 690577 A IE690577 A IE 690577A IE 57769 A IE57769 A IE 57769A IE 33116 L IE33116 L IE 33116L
- Authority
- IE
- Ireland
- Prior art keywords
- pyrryl
- rch
- acid
- phenyl
- compounds
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 1 - Pyrryl Chemical group 0.000 abstract 3
- 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
- YDUDSQOJLRADBS-UHFFFAOYSA-N 4-oxo-4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical class N1(C=CC=C1)C1=CC=C(C(=O)CCC(=O)O)C=C1 YDUDSQOJLRADBS-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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 1
- 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
1,264,367. 4 - [p - (1 - Pyrryl) phenyl] butyric and 3 - [p - (1 - pyrryl) benzoyl] propionic acids. J. R. GEIGY A.G. 28 April, 1969 [29 April, 1968; 20 Nov., 1968], No. 21523/69. Heading C2C. 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 R<SP>1</SP>CH(CO 2 Et) 2 , R<SP>1</SP>CH(CO 2 H) 2 and R<SP>1</SP>CH 2 CO 2 Et [where R<SP>1</SP>= 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.
[GB1264367A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE33116L true IE33116L (en) | 1969-10-29 |
| IE33116B1 IE33116B1 (en) | 1974-03-20 |
Family
ID=25699490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE577/69A IE33116B1 (en) | 1968-04-29 | 1969-04-28 | Process for the production of new substituted phenylalkanoic acids |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3651084A (en) |
| JP (2) | JPS4827309B1 (en) |
| AT (5) | AT286976B (en) |
| BE (1) | BE732301A (en) |
| BG (5) | BG15206A3 (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 DK DK219769AA patent/DK125132C/en active
- 1969-04-22 US US818393A patent/US3651084A/en not_active Expired - Lifetime
- 1969-04-22 NL NL6906209A patent/NL6906209A/xx unknown
- 1969-04-22 SE SE05684/69A patent/SE338994B/xx unknown
- 1969-04-22 FI FI691195A patent/FI50971C/en active
- 1969-04-28 ES ES366545A patent/ES366545A1/en not_active Expired
- 1969-04-28 IL IL6932089A patent/IL32089A/en unknown
- 1969-04-28 ES ES366546A patent/ES366546A1/en not_active Expired
- 1969-04-28 AT AT409069A patent/AT286976B/en active
- 1969-04-28 ES ES366544A patent/ES366544A1/en not_active Expired
- 1969-04-28 GB GB2152369A patent/GB1264367A/en not_active Expired
- 1969-04-28 DE DE19691921651 patent/DE1921651A1/en active Pending
- 1969-04-28 AT AT189170A patent/AT290518B/en not_active IP Right Cessation
- 1969-04-28 IE IE577/69A patent/IE33116B1/en unknown
- 1969-04-28 BG BG012132A patent/BG15206A3/en unknown
- 1969-04-28 PL PL1969133260A patent/PL69906B1/pl unknown
- 1969-04-28 CS CS7997*A patent/CS161852B2/cs unknown
- 1969-04-28 BG BG013039A patent/BG15547A3/en unknown
- 1969-04-28 AT AT189070A patent/AT290517B/en not_active IP Right Cessation
- 1969-04-28 ES ES366547A patent/ES366547A1/en not_active Expired
- 1969-04-28 CS CS7999*A patent/CS161854B2/cs unknown
- 1969-04-28 CS CS7998*A patent/CS161853B2/cs unknown
- 1969-04-28 AT AT189270A patent/AT290519B/en not_active IP Right Cessation
- 1969-04-28 CS CS3005A patent/CS161851B2/cs 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 BG013037A patent/BG15752A3/en unknown
- 1969-09-17 BG BG013040A patent/BG15548A3/en unknown
- 1969-09-17 BG BG013038A patent/BG15546A3/en unknown
-
1971
- 1971-10-22 JP JP46083856A patent/JPS4827309B1/ja active Pending
- 1971-10-22 JP JP46083858A patent/JPS4813550B1/ja active Pending
Also Published As
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