DE2525848C3 - Substituierte Amide der 3-Methyl-4phenyl-3-butensäure, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel - Google Patents
Substituierte Amide der 3-Methyl-4phenyl-3-butensäure, Verfahren zu ihrer Herstellung und sie enthaltende ArzneimittelInfo
- Publication number
- DE2525848C3 DE2525848C3 DE2525848A DE2525848A DE2525848C3 DE 2525848 C3 DE2525848 C3 DE 2525848C3 DE 2525848 A DE2525848 A DE 2525848A DE 2525848 A DE2525848 A DE 2525848A DE 2525848 C3 DE2525848 C3 DE 2525848C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- butenoic acid
- phenyl
- compound
- fructose
- 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
- 150000001408 amides Chemical class 0.000 title claims description 13
- NGJLFMBOFBKYHK-VQHVLOKHSA-N (e)-3-methyl-4-phenylbut-3-enoic acid Chemical compound OC(=O)CC(/C)=C/C1=CC=CC=C1 NGJLFMBOFBKYHK-VQHVLOKHSA-N 0.000 title description 25
- 238000000034 method Methods 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 41
- 229930091371 Fructose Natural products 0.000 description 23
- 239000005715 Fructose Substances 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 23
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 9
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 208000006575 hypertriglyceridemia Diseases 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 238000013222 sprague-dawley male rat Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 230000000055 hyoplipidemic effect Effects 0.000 description 2
- 230000000999 hypotriglyceridemic effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000035604 cholesterolaemia Effects 0.000 description 1
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- -1 diethylamide 3-methyl-4-phenyl-3-butenoic acid Chemical compound 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- VSHBKFZWSYFCND-UHFFFAOYSA-N n,n-diethyl-3-methyl-4-phenylbut-3-enamide Chemical compound CCN(CC)C(=O)CC(C)=CC1=CC=CC=C1 VSHBKFZWSYFCND-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007666 subchronic toxicity Effects 0.000 description 1
- 231100000195 subchronic toxicity Toxicity 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sampling And Sample Adjustment (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23797/74A IT1060551B (it) | 1974-06-10 | 1974-06-10 | Ammidi sostituite dell acido 3 metil 4 penil 3 butenoico aventi elevata azione ipolipemizzante |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2525848A1 DE2525848A1 (de) | 1975-12-11 |
| DE2525848B2 DE2525848B2 (de) | 1978-04-06 |
| DE2525848C3 true DE2525848C3 (de) | 1978-11-30 |
Family
ID=11210071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2525848A Expired DE2525848C3 (de) | 1974-06-10 | 1975-06-10 | Substituierte Amide der 3-Methyl-4phenyl-3-butensäure, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4053635A (esLanguage) |
| JP (1) | JPS5616142B2 (esLanguage) |
| BE (1) | BE830063A (esLanguage) |
| DE (1) | DE2525848C3 (esLanguage) |
| ES (1) | ES438350A1 (esLanguage) |
| FR (1) | FR2273520A1 (esLanguage) |
| GB (1) | GB1475644A (esLanguage) |
| IT (1) | IT1060551B (esLanguage) |
| SE (1) | SE7506576L (esLanguage) |
| ZA (1) | ZA753659B (esLanguage) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190674A (en) * | 1976-02-03 | 1980-02-26 | Burroughs Wellcome Co. | 3-Fluoro-N-cyclopropylcinnamide |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2937117A (en) * | 1953-06-19 | 1960-05-17 | Chimie Atomistique | Process for lowering high blood cholesterol levels |
| US3231469A (en) * | 1961-03-18 | 1966-01-25 | Istituto Biochimico Italiano | beta-benzalbutyramide as an anticholesterolemic agent |
| US3245878A (en) * | 1962-01-09 | 1966-04-12 | Frank M Berger | Methods for lowering blood cholesterol |
| US3626005A (en) * | 1967-07-14 | 1971-12-07 | Nat Distillers Chem Corp | Preparation of unsaturated acyl halides |
| FR2040181A1 (esLanguage) * | 1969-04-02 | 1971-01-22 | Lipha | |
| SE377113B (esLanguage) * | 1971-05-15 | 1975-06-23 | Ciba Geigy Ag | |
| DE2205732A1 (de) * | 1972-02-08 | 1973-08-16 | Thomae Gmbh Dr K | Neue 4-(4-biphenylyl)-butensaeurederivate |
-
1974
- 1974-06-10 IT IT23797/74A patent/IT1060551B/it active
-
1975
- 1975-06-06 ZA ZA00753659A patent/ZA753659B/xx unknown
- 1975-06-06 US US05/584,490 patent/US4053635A/en not_active Expired - Lifetime
- 1975-06-09 ES ES438350A patent/ES438350A1/es not_active Expired
- 1975-06-09 SE SE7506576A patent/SE7506576L/xx unknown
- 1975-06-09 JP JP6867675A patent/JPS5616142B2/ja not_active Expired
- 1975-06-10 BE BE157185A patent/BE830063A/xx unknown
- 1975-06-10 GB GB2482675A patent/GB1475644A/en not_active Expired
- 1975-06-10 FR FR7518062A patent/FR2273520A1/fr active Granted
- 1975-06-10 DE DE2525848A patent/DE2525848C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2273520B1 (esLanguage) | 1980-05-23 |
| JPS516938A (esLanguage) | 1976-01-20 |
| JPS5616142B2 (esLanguage) | 1981-04-14 |
| IT1060551B (it) | 1982-08-20 |
| ES438350A1 (es) | 1977-01-16 |
| ZA753659B (en) | 1976-05-26 |
| SE7506576L (sv) | 1975-12-11 |
| US4053635A (en) | 1977-10-11 |
| FR2273520A1 (fr) | 1976-01-02 |
| GB1475644A (en) | 1977-06-01 |
| DE2525848A1 (de) | 1975-12-11 |
| BE830063A (fr) | 1975-10-01 |
| DE2525848B2 (de) | 1978-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |