US2138628A - Hydroxy-ethoxy derivatives of - Google Patents
Hydroxy-ethoxy derivatives of Download PDFInfo
- Publication number
- US2138628A US2138628A US2138628DA US2138628A US 2138628 A US2138628 A US 2138628A US 2138628D A US2138628D A US 2138628DA US 2138628 A US2138628 A US 2138628A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- phenyl
- carboxylic acid
- derivatives
- 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 - Lifetime
Links
- -1 Hydroxy-ethoxy Chemical class 0.000 title description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 18
- 229940095076 benzaldehyde Drugs 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 14
- LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 10
- 230000001988 toxicity Effects 0.000 description 10
- 231100000419 toxicity Toxicity 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- YTRMTPPVNRALON-UHFFFAOYSA-N Cinchophen Chemical class N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 6
- 230000001747 exhibiting Effects 0.000 description 6
- 150000002440 hydroxy compounds Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000001225 therapeutic Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- QMQXAQUBDPFOSS-UHFFFAOYSA-N 2-phenyl-1H-quinoline-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C=CC1(C(=O)O)C1=CC=CC=C1 QMQXAQUBDPFOSS-UHFFFAOYSA-N 0.000 description 2
- RCZOGESGQUHUFE-UHFFFAOYSA-N 2-phenylquinolin-3-ol Chemical compound OC1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 RCZOGESGQUHUFE-UHFFFAOYSA-N 0.000 description 2
- SHNMAZJVVFUXAQ-UHFFFAOYSA-N 2H-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CC=CC2=C1 SHNMAZJVVFUXAQ-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- BCTQDJSUQUMAGA-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC2=C(C=CC=C2C(=C1)C(=O)O)OCCO Chemical class C1(=CC=CC=C1)C1=NC2=C(C=CC=C2C(=C1)C(=O)O)OCCO BCTQDJSUQUMAGA-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- XAPRFLSJBSXESP-UHFFFAOYSA-N Oxycinchophen Chemical class N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000009114 investigational therapy Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Definitions
- This invention relates to derivatives of 2- phenyl-quinolin-4-carboxylic acid and more particularly to hydroxy-alkyl hydroxy derivatives of the latter and methods of making same.
- Hydroxy compounds of the Z-phenylquinoline- 4-carboxylic acid are already known. The comparative pharmacological investigation of these compounds, however, shows that they possess the same toxicity to animals as the 2-phenylquinoline--carboxylic acid itself. The same applies to the alklated hydroxy compounds of said acid which do not differ in this respect from the nonalkylated hydroxy compounds nor from the 2- phenylquinoline-4-carboxylic acid.
- One object of this invention is to provide derivatives of hydroxy-Z-phenylquinoline-4-carboxylic acids which show considerably less toxicity than the hydroxy acids themselves but about the same therapeutical efiiciency. It has been found that the hydroxyalkylated derivatives of said hydroxy 2 phenylquinoline 4 carb-oxylic acids possess these valuable properties.
- Another object of this invention consists in producing said hydroxyalkylated hydroxy derivatives of said phenylquinoline-4-carboxylic acid.
- hydroxyalkyl hydroxyanilines are reacted with benzaldehyde and pyroracemic acid.
- EXAMPLE 1 2-phenyZ-6-hydroxyethomy quinolz'ne-el-carboxylic acid 24 grams of the hydroxyethylether of p-aminophenol are boiled in 150 cos. of alcohol with 16 grams of benzaldehyde for 30 minutes wherefrom a small amount of alcohol. The acid obtained forms an amorphous, light-brown, tasteless powder of the melting point 198 C.
- a Z-phenyl hydroxyethoxy-quinoline-l-carboxylic acid selected from the group consisting of 2-phenyl-(i-hydroxyethoxy-quinoline 4 carboxylic acids and 2-phenyl-8-hydroxyethoxyquinoline-4carboxylic acids, said acid exhibiting considerably less toxicity than the hydroxy-2- phenyl-quinoline-4-carboxylic acids.
- a method of producing hydroxy alkoxy derivatives of Z-phenyl quinolinel-carboxylic acid which comprises heating a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines with benzaldehyde and pyroracemic acid and isolating the reaction product.
- a method of producing hydroxy alkoxy derivatives of Z-phenyl quinoline-l-carboxylic acid which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy-anilines and benzaldehyde, and isolating the reaction product.
- a method of producing hydroxy alkoxy derivatives of 2-phenyl quinoline--carboxylic acid which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines and benzaldehyde in alcohol and isolating the reaction product.
- a method of producing hydroxy alkoxy derivatives of 2-pheny1 quinolinel-carboxylic acid which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the 0- and p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling off the alcohol and isolating and purifying the reaction product.
- a method of producing hydroxy alkoxy derivatives of 2-phenyl quinoline-l-carboxylic acid which comprises slowly adding pyroracemicacid to a boiling solution of a compound taken from the group consisting of the 0- and p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling off the alcohol, extracting the residue with aqueous sodium carbonate solution, acidifying the extract obtained and purifying the precipitate.
- a method of producing hydroxy alkoxy derivatives of Z-phenyl quinoline-l-carboxylic acid which comprises slowly adding pyroracemio acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling oi the alcohol, extracting the residue with aqueous sodium carbonate solution, acidifying the extract obtained, isolating the precipitate and recrystallizing the latter from aqueous alcohol.
Description
Patented Nov. 29, 1938 UNITED STATES HYDROXY-ETHOXY DERIVATIVES, or 2- PHENYLQUINOLINEJLCARBOXYLIG ACID ANDMETHOD or MAKING'SAME Paul Diedrich, Finkenkrug, Germany, assignor to Shering-Kahlbaum A. G., Berlin, Germany, a corporation of Germany No Drawing. Original application February 20,
1934, Serial No. 712,254. Divided and this application March 4, 1936, Serial No. 67,089. In Germany February 22, 1933 Claims.
This invention relates to derivatives of 2- phenyl-quinolin-4-carboxylic acid and more particularly to hydroxy-alkyl hydroxy derivatives of the latter and methods of making same.
This application is a division of my copending application Ser. No. 712,254, filed February 20, 1934, entitled I-Iydroxy alkoxy derivatives of 2-phenylquinoline-4-carboxy1ic acid and method of making same, now Patent No. 2,064,297, dated December 15, 1936.
Hydroxy compounds of the Z-phenylquinoline- 4-carboxylic acid are already known. The comparative pharmacological investigation of these compounds, however, shows that they possess the same toxicity to animals as the 2-phenylquinoline--carboxylic acid itself. The same applies to the alklated hydroxy compounds of said acid which do not differ in this respect from the nonalkylated hydroxy compounds nor from the 2- phenylquinoline-4-carboxylic acid.
One object of this invention is to provide derivatives of hydroxy-Z-phenylquinoline-4-carboxylic acids which show considerably less toxicity than the hydroxy acids themselves but about the same therapeutical efiiciency. It has been found that the hydroxyalkylated derivatives of said hydroxy 2 phenylquinoline 4 carb-oxylic acids possess these valuable properties.
Another object of this invention consists in producing said hydroxyalkylated hydroxy derivatives of said phenylquinoline-4-carboxylic acid. For this purpose hydroxyalkyl hydroxyanilines are reacted with benzaldehyde and pyroracemic acid.
The following are specific examples of the practice of the present invention:
EXAMPLE 1 2-phenyZ-6-hydroxyethomy quinolz'ne-el-carboxylic acid 24 grams of the hydroxyethylether of p-aminophenol are boiled in 150 cos. of alcohol with 16 grams of benzaldehyde for 30 minutes wherefrom a small amount of alcohol. The acid obtained forms an amorphous, light-brown, tasteless powder of the melting point 198 C.
EXAMPLE 2 crystallization from dilute alcohol a yellow crystal powder of the melting point of 190 C.
While I have described the present invention setting forth two specific embodiments thereof, it is to be understood that my invention is not limited thereto, but that the invention includes other specific compounds and the manufacture thereof. My invention is, therefore, not to be limited except by the claims appended hereto.
What 1' claim as my invention is:
1. Z-phenyl-S-hydroxyethoxy quinoline-l-carboxylic acid, exhibiting considerably less toxicity than the hydroxy-Z-phenyl quinoliniE-L-carboxylic acids, but being of about the same therapeutical value as the latter, and representing an amorphous, light-brown tasteless powder.
2. 2-phenyl-8-hydroxyethoxy quinolinel-carboxylic acid, exhibiting considerably less toxicity than the hydroxy-Z-phenyl quinolinel-carboxylic acids, but being of about the same therapeutical value as the latter, and representing a yellow crystalline material.
3. A Z-phenyl hydroxyethoxy-quinoline-l-carboxylic acid selected from the group consisting of 2-phenyl-(i-hydroxyethoxy-quinoline 4 carboxylic acids and 2-phenyl-8-hydroxyethoxyquinoline-4carboxylic acids, said acid exhibiting considerably less toxicity than the hydroxy-2- phenyl-quinoline-4-carboxylic acids.
4. A method of producing hydroxy alkoxy derivatives of Z-phenyl quinolinel-carboxylic acid which comprises heating a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines with benzaldehyde and pyroracemic acid and isolating the reaction product.
5. A method of producing hydroxy alkoxy derivatives of 2-phenyl quinoline-4-carboxylic acid,
which comprises heating a compound taken from the group consisting of the oand p-hydroxy-ethyl ethers of an amino phenol with benzaldehyde and pyroracemic acid and isolating the reaction product.
6. A method of producing hydroxy alkoxy derivatives of Z-phenyl quinoline-l-carboxylic acid which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy-anilines and benzaldehyde, and isolating the reaction product.
7. A method of producing hydroxy alkoxy derivatives of 2-phenyl quinoline--carboxylic acid which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines and benzaldehyde in alcohol and isolating the reaction product.
8. A method of producing hydroxy alkoxy derivatives of 2-pheny1 quinolinel-carboxylic acid, which comprises slowly adding pyroracemic acid to a boiling solution of a compound taken from the group consisting of the 0- and p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling off the alcohol and isolating and purifying the reaction product.
9. A method of producing hydroxy alkoxy derivatives of 2-phenyl quinoline-l-carboxylic acid, which comprises slowly adding pyroracemicacid to a boiling solution of a compound taken from the group consisting of the 0- and p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling off the alcohol, extracting the residue with aqueous sodium carbonate solution, acidifying the extract obtained and purifying the precipitate.
10. A method of producing hydroxy alkoxy derivatives of Z-phenyl quinoline-l-carboxylic acid, which comprises slowly adding pyroracemio acid to a boiling solution of a compound taken from the group consisting of the oand p-hydroxy alkoxy anilines and benzaldehyde in alcohol, continuing the boiling for several hours, distilling oi the alcohol, extracting the residue with aqueous sodium carbonate solution, acidifying the extract obtained, isolating the precipitate and recrystallizing the latter from aqueous alcohol.
PAUL DIEDRICH.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2138628A true US2138628A (en) | 1938-11-29 |
Family
ID=3429811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2138628D Expired - Lifetime US2138628A (en) | Hydroxy-ethoxy derivatives of |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2138628A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150047A (en) * | 1962-02-16 | 1964-09-22 | Roussel Uclaf | 4-[2'-(beta-dimethylaminoethoxycarbonyl)-phenylamino]-7-chloro-quinoline and its acidaddition salts |
-
0
- US US2138628D patent/US2138628A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150047A (en) * | 1962-02-16 | 1964-09-22 | Roussel Uclaf | 4-[2'-(beta-dimethylaminoethoxycarbonyl)-phenylamino]-7-chloro-quinoline and its acidaddition salts |
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