BE569078A - - Google Patents
Info
- Publication number
- BE569078A BE569078A BE569078DA BE569078A BE 569078 A BE569078 A BE 569078A BE 569078D A BE569078D A BE 569078DA BE 569078 A BE569078 A BE 569078A
- Authority
- BE
- Belgium
- Prior art keywords
- carbon atoms
- general formula
- radical
- salts
- hydrazine
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000011780 sodium chloride Substances 0.000 claims description 16
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 claims description 12
- -1 alicyclic hydrocarbon radical Chemical class 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000002429 hydrazines Chemical class 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 230000000875 corresponding Effects 0.000 claims description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 235000021355 Stearic acid Nutrition 0.000 claims description 5
- 235000020778 linoleic acid Nutrition 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 229940095076 benzaldehyde Drugs 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical class CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims 4
- 150000003254 radicals Chemical class 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 241000243251 Hydra Species 0.000 claims 1
- 101710042047 SELENOO Proteins 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005645 linoleyl group Chemical group 0.000 claims 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 1
- VCRYGHPVKURQMM-UHFFFAOYSA-N methane;platinum Chemical compound C.[Pt] VCRYGHPVKURQMM-UHFFFAOYSA-N 0.000 claims 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical class N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims 1
- 125000000913 palmityl 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])C([H])([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 1
- 101710023907 selenoo1 Proteins 0.000 claims 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 1
- 150000001875 compounds Chemical class 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- FWYYYCVVISASJO-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)NNC(C)C Chemical compound C(CCCCCCCCCCCCCCC)NNC(C)C FWYYYCVVISASJO-UHFFFAOYSA-N 0.000 description 2
- YHRKZKJRYBIOBV-MURFETPASA-N C(CCCCCCC\C=C/C\C=C/CCCCC)NNC(C)C Chemical compound C(CCCCCCC\C=C/C\C=C/CCCCC)NNC(C)C YHRKZKJRYBIOBV-MURFETPASA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- SSVSELJXJJCANX-UHFFFAOYSA-N hexadecanehydrazide Chemical compound CCCCCCCCCCCCCCCC(=O)NN SSVSELJXJJCANX-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- QLJHYCNPORXTNP-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)NN=C(C)C Chemical compound C(CCCCCCCCCCCCCCCCC)NN=C(C)C QLJHYCNPORXTNP-UHFFFAOYSA-N 0.000 description 1
- IZYHJQSLKZVJDT-KTKRTIGZSA-N C(CCCCCCC\C=C/CCCCCCCC)NNCC1=CC=CC=C1 Chemical compound C(CCCCCCC\C=C/CCCCCCCC)NNCC1=CC=CC=C1 IZYHJQSLKZVJDT-KTKRTIGZSA-N 0.000 description 1
- JTZBUEGREZVYMM-DOFZRALJSA-N C(CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)NNCC1=CC=CC=C1 Chemical compound C(CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)NNCC1=CC=CC=C1 JTZBUEGREZVYMM-DOFZRALJSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N Dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N Iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- 240000002049 Sambucus australis Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000001430 anti-depressive Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BYTFESSQUGDMQQ-UHFFFAOYSA-N octadecanehydrazide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NN BYTFESSQUGDMQQ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569078A true BE569078A (da) |
Family
ID=188174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569078D BE569078A (da) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569078A (da) |
-
0
- BE BE569078D patent/BE569078A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH375017A (fr) | Procédé de préparation de nouveaux dérivés de l'imidazole | |
| EP0155870B1 (fr) | 3-aminoazétidine, ses sels, procédé pour leur préparation et intermédiaires de synthèse | |
| BE569078A (da) | ||
| CA1313871C (fr) | Derives de l'acide (dihydro-2,3 oxo-2 benzofurannyl-3)-2 acetique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2560873A1 (fr) | Medicaments a base de derives de la piperidine, nouveaux derives de la piperidine et leurs procedes de preparation | |
| JPS635087A (ja) | （＋）−トランス−１ａ，２，３，４ａ，５，６−ヘキサヒドロ−９−ヒドロキシ−４−プロピル−４Ｈ−ナフト〔１，２−ｂ〕−１，４−オキサジンのキラル合成 | |
| CH620678A5 (en) | Process for the preparation of a derivative of piperidine | |
| CH668593A5 (fr) | Composes heterocycliques appartenant aux series indoliques et leur preparation. | |
| BE569077A (da) | ||
| BE569076A (da) | ||
| FR2465735A1 (fr) | Composes intermediaires pour la preparation de derives de la morphine, et leur procede de preparation | |
| CA1161444A (fr) | Procede de preparation de derives du cycloheptindolol et de leurs sels avec les acides | |
| BE566396A (da) | ||
| BE569079A (da) | ||
| BE568943A (da) | ||
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| FR2615853A1 (fr) | Nouveau procede pour la preparation de derives de la piperazine pharmacologiquement actifs, derives et nouveaux intermediaires obtenus | |
| BE482321A (da) | ||
| BE568394A (da) | ||
| BE666612A (da) | ||
| BE632613A (da) | ||
| BE590187A (da) | ||
| BE517764A (da) | ||
| CH397652A (fr) | Procédé de préparation de dérivés du cyclobutane | |
| BE594328A (da) |