BE897566A - Derives d'acides w-amines, leur preparation et utilisation ainsi que les compositions contenant ces derives. - Google Patents
Derives d'acides w-amines, leur preparation et utilisation ainsi que les compositions contenant ces derives. Download PDFInfo
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- BE897566A BE897566A BE0/211380A BE211380A BE897566A BE 897566 A BE897566 A BE 897566A BE 0/211380 A BE0/211380 A BE 0/211380A BE 211380 A BE211380 A BE 211380A BE 897566 A BE897566 A BE 897566A
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- 239000000203 mixture Substances 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 alkyl radical Chemical class 0.000 claims description 80
- 239000002253 acid Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000003786 synthesis reaction Methods 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 150000001408 amides Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000002825 nitriles Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 230000006870 function Effects 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- CEMZQHFVTGKVFJ-UHFFFAOYSA-N 2-(pentylamino)butanamide Chemical compound CCCCCNC(CC)C(N)=O CEMZQHFVTGKVFJ-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003951 lactams Chemical class 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- CXGRRZVQHJQEAM-UHFFFAOYSA-N 2-(pentylamino)hexanamide Chemical compound CCCCCNC(C(N)=O)CCCC CXGRRZVQHJQEAM-UHFFFAOYSA-N 0.000 claims description 4
- ADLAZGFLWMCKNT-UHFFFAOYSA-N 2-(pentylamino)pentanamide Chemical compound C(CCCC)NC(C(=O)N)CCC ADLAZGFLWMCKNT-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- IEYGRKYTLIDVNU-UHFFFAOYSA-N 2-(decylamino)hexanamide Chemical compound C(CCCCCCCCC)NC(C(=O)N)CCCC IEYGRKYTLIDVNU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000012661 Dyskinesia Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000001953 Hypotension Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- 239000000730 antalgic agent Substances 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 3
- 230000036543 hypotension Effects 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 206010027175 memory impairment Diseases 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000022925 sleep disturbance Diseases 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000000921 anthelmintic agent Substances 0.000 claims description 2
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical group [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 230000003387 muscular Effects 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 230000003236 psychic effect Effects 0.000 claims description 2
- 208000018198 spasticity Diseases 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims 1
- 235000019483 Peanut oil Nutrition 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 229940124339 anthelmintic agent Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims 1
- 229940093471 ethyl oleate Drugs 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 235000019198 oils Nutrition 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- 239000008223 sterile water Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000013256 coordination polymer Substances 0.000 description 8
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 6
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 5
- 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 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 206010010904 Convulsion Diseases 0.000 description 4
- 241001676573 Minium Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 150000004252 dithioacetals Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000002182 synaptic membrane Anatomy 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JSUKJSGJFFTJOL-UHFFFAOYSA-N 4-(2-phenylethylazaniumyl)butanoate Chemical compound OC(=O)CCCNCCC1=CC=CC=C1 JSUKJSGJFFTJOL-UHFFFAOYSA-N 0.000 description 2
- ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 2
- JSAWFGSXRPCFSW-UHFFFAOYSA-N 5-chloropentanenitrile Chemical compound ClCCCCC#N JSAWFGSXRPCFSW-UHFFFAOYSA-N 0.000 description 2
- YQMDXWJKIFPPEN-UHFFFAOYSA-N 6-chlorohexanamide Chemical compound NC(=O)CCCCCCl YQMDXWJKIFPPEN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229920000715 Mucilage Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004717 pyruvic acids Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU84343 | 1982-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE897566A true BE897566A (fr) | 1983-12-16 |
Family
ID=19729937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/211380A BE897566A (fr) | 1982-08-20 | 1983-08-19 | Derives d'acides w-amines, leur preparation et utilisation ainsi que les compositions contenant ces derives. |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5962555A (en, 2012) |
| KR (1) | KR870000980B1 (en, 2012) |
| AU (2) | AU1814083A (en, 2012) |
| BE (1) | BE897566A (en, 2012) |
| CA (1) | CA1256899A (en, 2012) |
| CH (1) | CH659466A5 (en, 2012) |
| DE (2) | DE3329628A1 (en, 2012) |
| DK (1) | DK373383A (en, 2012) |
| ES (2) | ES525031A0 (en, 2012) |
| FI (1) | FI832935A7 (en, 2012) |
| FR (1) | FR2531950B1 (en, 2012) |
| GB (1) | GB2126224B (en, 2012) |
| GR (1) | GR77444B (en, 2012) |
| IE (1) | IE55872B1 (en, 2012) |
| IL (1) | IL69543A (en, 2012) |
| IT (1) | IT1169767B (en, 2012) |
| MA (1) | MA19882A1 (en, 2012) |
| MX (1) | MX156348A (en, 2012) |
| NL (1) | NL8302916A (en, 2012) |
| NO (1) | NO163770C (en, 2012) |
| OA (1) | OA07525A (en, 2012) |
| PT (1) | PT77226B (en, 2012) |
| SE (1) | SE8304513L (en, 2012) |
| ZA (1) | ZA836130B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6288120B1 (en) | 1996-12-20 | 2001-09-11 | Pfizer Inc. | Prevention of loss and restoration of bone mass by certain prostaglandin agonists |
| US7442702B2 (en) | 1997-10-10 | 2008-10-28 | Pfizer Inc. | Prostaglandin agonists |
| FR3018076A1 (fr) * | 2014-03-03 | 2015-09-04 | Arkema France | Procede de preparation de derives de l'acide 11-aminoundecanoique et de l'acide 12-aminododecanoique |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3476197D1 (en) * | 1983-08-01 | 1989-02-23 | Mclean Hospital Corp | Gaba esters and gaba analogue esters |
| DE3445816C1 (de) | 1984-12-15 | 1986-06-12 | Behringwerke Ag, 3550 Marburg | Flaechenfoermiges diagnostisches Mittel |
| GB8813185D0 (en) * | 1988-06-03 | 1988-07-06 | Wyeth John & Brother Ltd | New method & amines used therein |
| CA2028782C (en) * | 1989-11-07 | 2003-10-14 | Christian T. Goralski | Process for the production of vinyl-gaba |
| US5585358A (en) * | 1993-07-06 | 1996-12-17 | Yissum Research Development Corporation Of The Hebrew University Of Jerusalem | Derivatives of valproic acid amides and 2-valproenoic acid amides, method of making and use thereof as anticonvulsant agents |
| ES2200184T7 (es) | 1996-07-24 | 2015-02-10 | Warner-Lambert Company Llc | Isobutilgaba y sus derivados para el tratamiento del dolor |
| FR2753967B1 (fr) * | 1996-09-27 | 1998-11-27 | Sod Conseils Rech Applic | Nouveaux derives de la phenoxyethylamine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| CA2416821A1 (en) | 2000-07-21 | 2002-01-31 | Teva Pharmaceutical Industries, Ltd. | Use of derivatives of valproic acid and 2-valproenic acid amides for the treatment of mania in bipolar disorder |
| WO2002042256A2 (en) * | 2000-11-21 | 2002-05-30 | Ucb, S.A. | N-alkylated gaba compounds, processes for their preparation and their use as medicaments |
| US7504538B2 (en) | 2003-10-16 | 2009-03-17 | Cara Therapeutics, Inc. | Amide or thioamide derivatives and their use in the treatment of pain |
| WO2020031201A1 (en) * | 2018-08-04 | 2020-02-13 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of 6-aminohexanoic acid |
| CN109593044B (zh) * | 2018-12-06 | 2021-05-14 | 盐城工学院 | 一种烷基脂肪酸胺及其制备方法 |
| CN115636761B (zh) * | 2021-07-20 | 2024-07-05 | 中国石油天然气股份有限公司 | 一种油溶性表面活性剂、驱油剂及其应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE636245A (en, 2012) | ||||
| GB586645A (en) * | 1944-07-19 | 1947-03-26 | Burroughs Wellcome Co | Improvements relating to the synthesis of amino acid derivatives and salts thereof |
| GB775364A (en) * | 1954-05-05 | 1957-05-22 | Unilever Ltd | Improvements in soap compositions |
| US2851345A (en) * | 1955-02-02 | 1958-09-09 | Armour & Co | Fuel oil compositions |
| DE1189556B (de) * | 1962-05-29 | 1965-03-25 | Sandoz Ag | Verfahren zur Herstellung von 3-Diaethylaminobuttersaeure-N-methylanilid |
| BE647556A (en, 2012) * | 1964-05-06 | 1964-08-31 | ||
| IE33790B1 (en) * | 1968-06-04 | 1974-10-30 | Beecham Group Ltd | Derivatives of n-acylaminoacid amides |
| US3954778A (en) * | 1970-03-03 | 1976-05-04 | Zambon S.P.A. | Aminoacetyl derivatives of 2,3-diphenyl cyclopropyl amine |
| GB1369247A (en) * | 1970-08-07 | 1974-10-02 | Pfizer | Amines the preparation thereof and their use in pharmaceutical compositions |
| DE2234399A1 (de) * | 1972-07-17 | 1974-01-31 | Thomae Gmbh Dr K | Hautschutzmittel |
| US3947579A (en) | 1974-06-03 | 1976-03-30 | Nelson Research & Development Company | Method and composition for potentiating neuroleptic drugs |
| GB1538207A (en) * | 1975-12-09 | 1979-01-10 | Mitsubishi Chem Ind | N2-arylsulphonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| LU78804A1 (de) * | 1977-12-30 | 1979-07-20 | Byk Gulden Lomberg Chem Fab | N-substituierte w-aminoalkanoyl-w-aminoalkansaeuren,ihre verwendung und verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| LU78805A1 (de) * | 1977-12-30 | 1979-07-20 | Byk Gulden Lomberg Chem Fab | Acylhydrocarbylaminoalkansaeuren,ihre herstellung und verwendung sowie sie enthaltende arzneimittel |
| DE3050800C2 (en, 2012) * | 1979-03-22 | 1989-06-22 | Continental Pharma Inc., Bruessel/Bruxelles, Be |
-
1983
- 1983-08-16 FI FI832935A patent/FI832935A7/fi not_active Application Discontinuation
- 1983-08-16 DK DK373383A patent/DK373383A/da not_active Application Discontinuation
- 1983-08-17 CA CA000434769A patent/CA1256899A/en not_active Expired
- 1983-08-17 DE DE19833329628 patent/DE3329628A1/de active Granted
- 1983-08-17 DE DE3347867A patent/DE3347867C2/de not_active Expired
- 1983-08-18 IE IE1933/83A patent/IE55872B1/en unknown
- 1983-08-18 GR GR72245A patent/GR77444B/el unknown
- 1983-08-18 GB GB08322245A patent/GB2126224B/en not_active Expired
- 1983-08-18 NO NO832965A patent/NO163770C/no unknown
- 1983-08-19 MX MX198462A patent/MX156348A/es unknown
- 1983-08-19 IT IT22591/83A patent/IT1169767B/it active
- 1983-08-19 AU AU18140/83A patent/AU1814083A/en not_active Abandoned
- 1983-08-19 ZA ZA836130A patent/ZA836130B/xx unknown
- 1983-08-19 CH CH4544/83A patent/CH659466A5/fr not_active IP Right Cessation
- 1983-08-19 PT PT77226A patent/PT77226B/pt not_active IP Right Cessation
- 1983-08-19 BE BE0/211380A patent/BE897566A/fr not_active IP Right Cessation
- 1983-08-19 OA OA58092A patent/OA07525A/xx unknown
- 1983-08-19 FR FR8313490A patent/FR2531950B1/fr not_active Expired
- 1983-08-19 SE SE8304513A patent/SE8304513L/xx not_active Application Discontinuation
- 1983-08-19 NL NL8302916A patent/NL8302916A/nl not_active Application Discontinuation
- 1983-08-19 ES ES525031A patent/ES525031A0/es active Granted
- 1983-08-20 KR KR1019830003898A patent/KR870000980B1/ko not_active Expired
- 1983-08-20 JP JP58150964A patent/JPS5962555A/ja active Granted
- 1983-08-20 MA MA20104A patent/MA19882A1/fr unknown
- 1983-08-22 IL IL69543A patent/IL69543A/xx unknown
-
1985
- 1985-09-02 ES ES546625A patent/ES8800658A1/es not_active Expired
-
1988
- 1988-04-18 AU AU14727/88A patent/AU1472788A/en not_active Abandoned
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6288120B1 (en) | 1996-12-20 | 2001-09-11 | Pfizer Inc. | Prevention of loss and restoration of bone mass by certain prostaglandin agonists |
| US6492412B2 (en) | 1996-12-20 | 2002-12-10 | Pfizer, Inc. | Prevention of loss and restoration of bone mass by certain prostaglandin agonists |
| US6649657B2 (en) | 1996-12-20 | 2003-11-18 | Pfizer Inc. | Prevention of loss and restoration of bone mass by certain prostaglandin agonists |
| US6998423B2 (en) | 1996-12-20 | 2006-02-14 | Pfizer Inc. | Prevention of loss and restoration of bone mass by certain prostaglandin agonists |
| US7442702B2 (en) | 1997-10-10 | 2008-10-28 | Pfizer Inc. | Prostaglandin agonists |
| FR3018076A1 (fr) * | 2014-03-03 | 2015-09-04 | Arkema France | Procede de preparation de derives de l'acide 11-aminoundecanoique et de l'acide 12-aminododecanoique |
| WO2015132519A1 (fr) | 2014-03-03 | 2015-09-11 | Arkema France | Procédé de préparation de dérives de l'acide 11-aminoundecanoique et de l'acide 12-aminododecanoique |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CH | Change of patent owner |
Owner name: *CONTINENTAL PHARMA INC. Effective date: 19840523 |
|
| RE | Patent lapsed |
Owner name: CONTINENTAL PHARMA INC. Effective date: 19840819 |