CY1294A - Fatty acid amide and hydrazide derivatives their production and use as pharmaceuticals - Google Patents
Fatty acid amide and hydrazide derivatives their production and use as pharmaceuticals Download PDFInfo
- Publication number
- CY1294A CY1294A CY1294A CY129479A CY1294A CY 1294 A CY1294 A CY 1294A CY 1294 A CY1294 A CY 1294A CY 129479 A CY129479 A CY 129479A CY 1294 A CY1294 A CY 1294A
- Authority
- CY
- Cyprus
- Prior art keywords
- hydrogen
- cis
- formula
- alkoxy
- radical
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 title description 2
- 239000000194 fatty acid Substances 0.000 title description 2
- 229930195729 fatty acid Natural products 0.000 title description 2
- 150000004665 fatty acids Chemical class 0.000 title description 2
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
- -1 cyclopropanyl group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Chemical group 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 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 31
- 150000002431 hydrogen Chemical class 0.000 description 17
- 235000012000 cholesterol Nutrition 0.000 description 15
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 13
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 13
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 13
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 235000021313 oleic acid Nutrition 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- PDXZQLDUVAKMBQ-UHFFFAOYSA-N (1R*,2R*)-2-Octylcyclopropaneoctanoic acid Natural products CCCCCCCCC1CC1CCCCCCCC(O)=O PDXZQLDUVAKMBQ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000001840 cholesterol esters Chemical class 0.000 description 5
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 5
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010089254 Cholesterol oxidase Proteins 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 235000021319 Palmitoleic acid Nutrition 0.000 description 2
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- DABYEOZXRSTEGL-UHFFFAOYSA-N ethyl 2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OCC)=CNC2=C1 DABYEOZXRSTEGL-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- QSICYEZVNJWHKP-HZJYTTRNSA-N (9z,12z)-n-(2,3-dihydro-1h-inden-1-yl)octadeca-9,12-dienamide Chemical compound C1=CC=C2C(NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)CCC2=C1 QSICYEZVNJWHKP-HZJYTTRNSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- UUVQFCZCCXCYHF-UHFFFAOYSA-N 1-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole Chemical compound C1CCCC2N(O)CCC21 UUVQFCZCCXCYHF-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PDXZQLDUVAKMBQ-QZTJIDSGSA-N 8-[(1r,2r)-2-octylcyclopropyl]octanoic acid Chemical compound CCCCCCCC[C@@H]1C[C@H]1CCCCCCCC(O)=O PDXZQLDUVAKMBQ-QZTJIDSGSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- AUQRTKXTDKXTMI-KTKRTIGZSA-N CCCCCCCC/C=C\CCCCCCCCNC1C2=CC=CC=C2CC1 Chemical compound CCCCCCCC/C=C\CCCCCCCCNC1C2=CC=CC=C2CC1 AUQRTKXTDKXTMI-KTKRTIGZSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- RJFDERYBUXRTTM-DOFZRALJSA-N N-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl]-2,3-dihydro-1H-inden-1-amine Chemical compound CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNC1CCC2=CC=CC=C12 RJFDERYBUXRTTM-DOFZRALJSA-N 0.000 description 1
- IFGJWBRDWIINJX-KTKRTIGZSA-N N-[(Z)-octadec-9-enyl]-2,3-dihydro-1H-inden-2-amine Chemical compound CCCCCCCC/C=C\CCCCCCCCNC1CC2=CC=CC=C2C1 IFGJWBRDWIINJX-KTKRTIGZSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 108010059712 Pronase Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102000000019 Sterol Esterase Human genes 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- MSJHOJKVMMEMNX-UHFFFAOYSA-N benzylhydrazine;hydron;dichloride Chemical compound Cl.Cl.NNCC1=CC=CC=C1 MSJHOJKVMMEMNX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000251 cholesterol ester accumulation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PESYCVVSLYSXAK-UHFFFAOYSA-N ethyl 2-amino-3-(1h-indol-3-yl)propanoate;hydron;chloride Chemical compound Cl.C1=CC=C2C(CC(N)C(=O)OCC)=CNC2=C1 PESYCVVSLYSXAK-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003516 hyperlipidaemic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000003000 inclusion body Anatomy 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000007758 minimum essential medium Substances 0.000 description 1
- OZMPMDGGUDJJGT-DXKPHZOSSA-N n-(2,3-dihydro-1h-inden-1-yl)-8-[(1r,2r)-2-[[(1s,2s)-2-pentylcyclopropyl]methyl]cyclopropyl]octanamide Chemical compound CCCCC[C@H]1C[C@H]1C[C@@H]1[C@H](CCCCCCCC(=O)NC2C3=CC=CC=C3CC2)C1 OZMPMDGGUDJJGT-DXKPHZOSSA-N 0.000 description 1
- ACSZHVIBQIYJSL-FQUZAXHOSA-N n-(2-methylphenyl)-8-[(1r,2r)-2-[[(1s,2s)-2-pentylcyclopropyl]methyl]cyclopropyl]octanamide Chemical compound CCCCC[C@H]1C[C@H]1C[C@@H]1[C@H](CCCCCCCC(=O)NC=2C(=CC=CC=2)C)C1 ACSZHVIBQIYJSL-FQUZAXHOSA-N 0.000 description 1
- LXVKDQMPXIBDEI-BJKOFHAPSA-N n-(2-methylphenyl)-8-[(1r,2s)-2-octylcyclopropyl]octanamide Chemical compound CCCCCCCC[C@H]1C[C@H]1CCCCCCCC(=O)NC1=CC=CC=C1C LXVKDQMPXIBDEI-BJKOFHAPSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B22/00—Use of inorganic materials as active ingredients for mortars, concrete or artificial stone, e.g. accelerators or shrinkage compensating agents
- C04B22/0013—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
- C07D209/20—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 substituted additionally by nitrogen atoms, e.g. tryptophane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ceramic Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Vascular Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86781378A | 1978-01-09 | 1978-01-09 | |
| US86782478A | 1978-01-09 | 1978-01-09 | |
| US87283678A | 1978-01-27 | 1978-01-27 | |
| US88178178A | 1978-02-27 | 1978-02-27 | |
| US05/881,780 US4229463A (en) | 1978-02-27 | 1978-02-27 | Unsaturated fatty acid hydrazides |
| US05/891,298 US4194002A (en) | 1978-03-29 | 1978-03-29 | Cholesterol ester-reducing amides of hexahydroindolinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1294A true CY1294A (en) | 1985-10-18 |
Family
ID=27560330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1294A CY1294A (en) | 1978-01-09 | 1979-01-05 | Fatty acid amide and hydrazide derivatives their production and use as pharmaceuticals |
Country Status (20)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937175A1 (de) * | 1978-09-18 | 1980-03-27 | Sandoz Ag | Sekundaere amide von 2-alkynoylsaeuren, deren herstellung und deren pharmazeutischen zusammensetzungen |
| US4297349A (en) | 1980-04-15 | 1981-10-27 | Sandoz, Inc. | Silicon-bearing carboxylic acids and amides |
| US4722927A (en) * | 1986-04-28 | 1988-02-02 | Warner-Lambert Company | Pyrimidine amides of oleic or linoleic acid, composition containing them and their use as inhibitors of acyl-CoA cholesterol acyltransferase |
| FR2633617B1 (fr) * | 1988-07-04 | 1991-02-08 | Adir | Nouveaux derives du benzocycloheptene, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| US5290814A (en) * | 1988-11-21 | 1994-03-01 | Burroughs Wellcome Co. | Anti-atherosclerotic diaryl compounds |
| WO2009132051A1 (en) * | 2008-04-21 | 2009-10-29 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1814334B2 (de) * | 1967-12-21 | 1973-04-19 | Sumitomo Chemical Co Ltd , Osaka (Japan) | Fettsaeureamide und diese verbindungen enthaltende arzneimittel |
| FR2000945A1 (enrdf_load_html_response) * | 1968-01-30 | 1969-09-19 | Sumitomo Chemical Co | |
| JPS5835505B2 (ja) * | 1976-01-09 | 1983-08-03 | エーザイ株式会社 | Ｎ−（α−メチル−ベンジル）−脂肪酸アミド |
-
1978
- 1978-12-30 DE DE19782856856 patent/DE2856856A1/de not_active Ceased
-
1979
- 1979-01-02 CH CH379A patent/CH644842A5/de not_active IP Right Cessation
- 1979-01-03 DK DK3079A patent/DK3079A/da not_active Application Discontinuation
- 1979-01-04 IT IT19059/79A patent/IT1110603B/it active
- 1979-01-04 FI FI790025A patent/FI790025A7/fi not_active IP Right Cessation
- 1979-01-05 GB GB79337A patent/GB2012261B/en not_active Expired
- 1979-01-05 CY CY1294A patent/CY1294A/en unknown
- 1979-01-08 SE SE7900142A patent/SE446093B/sv not_active IP Right Cessation
- 1979-01-08 CA CA319,259A patent/CA1101871A/en not_active Expired
- 1979-01-08 IL IL56393A patent/IL56393A/xx unknown
- 1979-01-08 NZ NZ189331A patent/NZ189331A/xx unknown
- 1979-01-08 IE IE31/79A patent/IE48077B1/en unknown
- 1979-01-08 JP JP13879A patent/JPS54109930A/ja active Granted
- 1979-01-09 AU AU43233/79A patent/AU529328B2/en not_active Ceased
- 1979-01-09 FR FR7900438A patent/FR2416885A1/fr active Granted
- 1979-01-09 PT PT69052A patent/PT69052A/pt unknown
-
1985
- 1985-06-01 SG SG42985A patent/SG42985G/en unknown
- 1985-06-19 KE KE3546A patent/KE3546A/xx unknown
- 1985-10-17 HK HK809/85A patent/HK80985A/xx unknown
- 1985-12-30 MY MY133/85A patent/MY8500133A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KE3546A (en) | 1985-07-19 |
| FI790025A7 (fi) | 1979-07-10 |
| JPS54109930A (en) | 1979-08-29 |
| IT7919059A0 (it) | 1979-01-04 |
| AU529328B2 (en) | 1983-06-02 |
| NZ189331A (en) | 1981-07-13 |
| DE2856856A1 (de) | 1979-07-12 |
| CA1101871A (en) | 1981-05-26 |
| SE446093B (sv) | 1986-08-11 |
| IE790031L (en) | 1979-07-09 |
| JPS6323987B2 (enrdf_load_html_response) | 1988-05-18 |
| HK80985A (en) | 1985-10-25 |
| IL56393A (en) | 1982-08-31 |
| SE7900142L (sv) | 1979-07-10 |
| AU4323379A (en) | 1979-07-19 |
| IE48077B1 (en) | 1984-09-19 |
| FR2416885A1 (fr) | 1979-09-07 |
| FR2416885B1 (enrdf_load_html_response) | 1983-04-22 |
| IL56393A0 (en) | 1979-03-12 |
| IT1110603B (it) | 1985-12-23 |
| SG42985G (en) | 1985-12-13 |
| DK3079A (da) | 1979-07-10 |
| PT69052A (fr) | 1979-02-01 |
| MY8500133A (en) | 1985-12-31 |
| GB2012261A (en) | 1979-07-25 |
| CH644842A5 (de) | 1984-08-31 |
| GB2012261B (en) | 1982-12-22 |
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