DE249241C - - Google Patents
Info
- Publication number
- DE249241C DE249241C DE1910249241D DE249241DA DE249241C DE 249241 C DE249241 C DE 249241C DE 1910249241 D DE1910249241 D DE 1910249241D DE 249241D A DE249241D A DE 249241DA DE 249241 C DE249241 C DE 249241C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- acids
- parts
- acid
- arylated
- 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 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- FZLGYKHVAWMWOS-UHFFFAOYSA-N 1-ethyl-1-(2-phenylethyl)urea Chemical compound C1(=CC=CC=C1)CCN(C(=O)N)CC FZLGYKHVAWMWOS-UHFFFAOYSA-N 0.000 description 1
- KDYOFXPLHVSIHS-UHFFFAOYSA-N 2-(4-methylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(C)C=C1 KDYOFXPLHVSIHS-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- GGDSSEUHMYLPTL-UHFFFAOYSA-N 5-methyl-2-phenylhexanenitrile Chemical compound CC(C)CCC(C#N)C1=CC=CC=C1 GGDSSEUHMYLPTL-UHFFFAOYSA-N 0.000 description 1
- GUZQYASIYUFLIN-UHFFFAOYSA-N 5-methyl-N-phenylhexanamide Chemical compound CC(C)CCCC(=O)NC1=CC=CC=C1 GUZQYASIYUFLIN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CQFIHZMYFNTQOH-UHFFFAOYSA-N CCC(CC)O.Br Chemical compound CCC(CC)O.Br CQFIHZMYFNTQOH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE249241T | 1910-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE249241C true DE249241C (enrdf_load_stackoverflow) | 1912-07-13 |
Family
ID=33304721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1910249241D Expired DE249241C (enrdf_load_stackoverflow) | 1910-05-01 | 1910-05-01 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE249241C (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681928A (en) * | 1948-12-22 | 1954-06-22 | Abbott Lab | Alpha-phenylisobutyrylurea |
| DE1122958B (de) * | 1955-06-23 | 1962-02-01 | Pharmacia Ab | Verfahren zur Herstellung von N,N-disubstituierten Arylessigsaeureamiden |
| WO2000058293A3 (en) * | 1999-03-29 | 2001-01-25 | Hoffmann La Roche | Glucokinase activators |
| US6320050B1 (en) | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
| US6528543B1 (en) | 1999-03-29 | 2003-03-04 | Hoffman-La Roche Inc. | Urea derivatives |
| US6610846B1 (en) | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| US7105671B2 (en) | 2002-04-26 | 2006-09-12 | Hoffmann-La Roche Inc. | Substituted-cycloalkyl and oxygenated-cycloalkyl glucokinase activators |
| US7132425B2 (en) | 2002-12-12 | 2006-11-07 | Hoffmann-La Roche Inc. | 5-substituted-six-membered heteroaromatic glucokinase activators |
-
1910
- 1910-05-01 DE DE1910249241D patent/DE249241C/de not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681928A (en) * | 1948-12-22 | 1954-06-22 | Abbott Lab | Alpha-phenylisobutyrylurea |
| DE1122958B (de) * | 1955-06-23 | 1962-02-01 | Pharmacia Ab | Verfahren zur Herstellung von N,N-disubstituierten Arylessigsaeureamiden |
| WO2000058293A3 (en) * | 1999-03-29 | 2001-01-25 | Hoffmann La Roche | Glucokinase activators |
| US6320050B1 (en) | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
| US6528543B1 (en) | 1999-03-29 | 2003-03-04 | Hoffman-La Roche Inc. | Urea derivatives |
| US6610846B1 (en) | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| RU2242469C2 (ru) * | 1999-03-29 | 2004-12-20 | Ф.Хоффманн-Ля Рош Аг | Активаторы глюкокиназы |
| US6951945B2 (en) | 1999-03-29 | 2005-10-04 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| CZ301366B6 (cs) * | 1999-03-29 | 2010-02-03 | F. Hoffmann-La Roche Ag | 2-Fenyl-3-cykloalkylpropionamidová sloucenina, zpusob její prípravy a farmaceutický prostredek s jejím obsahem |
| US7105671B2 (en) | 2002-04-26 | 2006-09-12 | Hoffmann-La Roche Inc. | Substituted-cycloalkyl and oxygenated-cycloalkyl glucokinase activators |
| US7259166B2 (en) | 2002-04-26 | 2007-08-21 | Hoffmann-La Roche Inc. | Substituted-cycloalkyl and oxygenated-cycloalkyl glucokinase activators |
| US7132425B2 (en) | 2002-12-12 | 2006-11-07 | Hoffmann-La Roche Inc. | 5-substituted-six-membered heteroaromatic glucokinase activators |
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