BE569077A - - Google Patents
Info
- Publication number
- BE569077A BE569077A BE569077DA BE569077A BE 569077 A BE569077 A BE 569077A BE 569077D A BE569077D A BE 569077DA BE 569077 A BE569077 A BE 569077A
- Authority
- BE
- Belgium
- Prior art keywords
- hydrazine
- radical
- salts
- acid
- general formula
- Prior art date
Links
- -1 alicyclic hydrocarbon radical Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002429 hydrazines Chemical class 0.000 claims description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 150000007857 hydrazones Chemical class 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 4
- FWWDFDMCZLOXQI-UHFFFAOYSA-N pivhydrazine Chemical compound CC(C)(C)C(=O)NNCC1=CC=CC=C1 FWWDFDMCZLOXQI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- WZHVHIZNXIZYCW-UHFFFAOYSA-N n'-propan-2-ylcyclohexanecarbohydrazide Chemical compound CC(C)NNC(=O)C1CCCCC1 WZHVHIZNXIZYCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- PTGXSXYMEHNCCN-UHFFFAOYSA-N 2-methyl-n'-propan-2-ylpropanehydrazide Chemical compound CC(C)NNC(=O)C(C)C PTGXSXYMEHNCCN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- IEMAUAQJNPHUBQ-UHFFFAOYSA-N n'-benzylcyclohexanecarbohydrazide Chemical compound C1CCCCC1C(=O)NNCC1=CC=CC=C1 IEMAUAQJNPHUBQ-UHFFFAOYSA-N 0.000 claims description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 6
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical class CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- MUQNAPSBHXFMHT-UHFFFAOYSA-N tert-butylhydrazine Chemical class CC(C)(C)NN MUQNAPSBHXFMHT-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000155 melt Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- OARJXUPBZNUYBG-UHFFFAOYSA-N 2,2-dimethylpropanehydrazide Chemical compound CC(C)(C)C(=O)NN OARJXUPBZNUYBG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CGWBFZCBNLMLDT-UHFFFAOYSA-N N'-propan-2-ylcyclobutanecarbohydrazide Chemical compound C1(CCC1)C(=O)NNC(C)C CGWBFZCBNLMLDT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- PRBLRLQZOKOQCQ-UHFFFAOYSA-N benzylhydrazine;hydron;chloride Chemical compound Cl.NNCC1=CC=CC=C1 PRBLRLQZOKOQCQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- SYMQJSAALKSMDI-UHFFFAOYSA-N n'-propan-2-ylcyclopropanecarbohydrazide Chemical compound CC(C)NNC(=O)C1CC1 SYMQJSAALKSMDI-UHFFFAOYSA-N 0.000 description 2
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XLUXAKJPHJEFKL-UHFFFAOYSA-N 1-ethylcyclobutane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCC1 XLUXAKJPHJEFKL-UHFFFAOYSA-N 0.000 description 1
- BUWSHNOMVQKVHJ-UHFFFAOYSA-N 2,2-dimethyl-n'-(2-methylpropyl)propanehydrazide Chemical compound CC(C)CNNC(=O)C(C)(C)C BUWSHNOMVQKVHJ-UHFFFAOYSA-N 0.000 description 1
- ADPTWQGNSDWONP-UHFFFAOYSA-N 2,2-dimethyl-n'-propan-2-ylpropanehydrazide Chemical compound CC(C)NNC(=O)C(C)(C)C ADPTWQGNSDWONP-UHFFFAOYSA-N 0.000 description 1
- AFFCNKPXUVCCSV-UHFFFAOYSA-N 2-ethyl-N-(propan-2-ylideneamino)hexanamide Chemical compound C(C)C(C(=O)NN=C(C)C)CCCC AFFCNKPXUVCCSV-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-M 2-ethylhexanoate Chemical compound CCCCC(CC)C([O-])=O OBETXYAYXDNJHR-UHFFFAOYSA-M 0.000 description 1
- PLNNJQXIITYYTN-UHFFFAOYSA-N 2-methylpropanehydrazide Chemical compound CC(C)C(=O)NN PLNNJQXIITYYTN-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- IFSYMERPHZDWPL-UHFFFAOYSA-N C(C)C(C(=O)NNC(C)C)(CC)CC Chemical compound C(C)C(C(=O)NNC(C)C)(CC)CC IFSYMERPHZDWPL-UHFFFAOYSA-N 0.000 description 1
- YUCKNZJSEIGEHP-UHFFFAOYSA-N C(C)C(C(=O)NNC(C)C)CCCC Chemical compound C(C)C(C(=O)NNC(C)C)CCCC YUCKNZJSEIGEHP-UHFFFAOYSA-N 0.000 description 1
- QMODKXQTPXEKIX-UHFFFAOYSA-N C1(CCC1)C(=O)NN=CC1=CC=CC=C1 Chemical compound C1(CCC1)C(=O)NN=CC1=CC=CC=C1 QMODKXQTPXEKIX-UHFFFAOYSA-N 0.000 description 1
- SVWIQAGGCZRETE-UHFFFAOYSA-N CC(C(=O)C(CC1=CC=CC=C1)NN)(C)C Chemical compound CC(C(=O)C(CC1=CC=CC=C1)NN)(C)C SVWIQAGGCZRETE-UHFFFAOYSA-N 0.000 description 1
- QRMGNDAWPXZGGM-UHFFFAOYSA-N CC(C(=O)NNC(C)C)(CC)C Chemical compound CC(C(=O)NNC(C)C)(CC)C QRMGNDAWPXZGGM-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- MQHWOCDLCIPJNH-UHFFFAOYSA-N N'-benzylcyclobutanecarbohydrazide Chemical compound C1(CCC1)C(=O)NNCC1=CC=CC=C1 MQHWOCDLCIPJNH-UHFFFAOYSA-N 0.000 description 1
- LLQGNFNOLKUJFN-UHFFFAOYSA-N N'-ethyl-2-methylpropanehydrazide Chemical compound C(C(C)C)(=O)NNCC LLQGNFNOLKUJFN-UHFFFAOYSA-N 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- KYUUPPKLZSVGMG-UHFFFAOYSA-N cyclobutanecarbohydrazide Chemical compound NNC(=O)C1CCC1 KYUUPPKLZSVGMG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HHEIMYAXCOIQCJ-UHFFFAOYSA-N ethyl 2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)C HHEIMYAXCOIQCJ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 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
- 239000012452 mother liquor Substances 0.000 description 1
- KFQQEKCFTGBATQ-UHFFFAOYSA-N n'-benzylcyclopropanecarbohydrazide Chemical compound C1CC1C(=O)NNCC1=CC=CC=C1 KFQQEKCFTGBATQ-UHFFFAOYSA-N 0.000 description 1
- DDJCJUZIYUNJLV-UHFFFAOYSA-N n-(benzylideneamino)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NN=CC1=CC=CC=C1 DDJCJUZIYUNJLV-UHFFFAOYSA-N 0.000 description 1
- RZAZJATVXHBINF-UHFFFAOYSA-N n-(propan-2-ylideneamino)cyclobutanecarboxamide Chemical compound CC(C)=NNC(=O)C1CCC1 RZAZJATVXHBINF-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
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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 |
|---|---|
| BE569077A true BE569077A (fi) |
Family
ID=188173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569077D BE569077A (fi) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569077A (fi) |
-
0
- BE BE569077D patent/BE569077A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH375017A (fr) | Procédé de préparation de nouveaux dérivés de l'imidazole | |
| EP0002978B1 (fr) | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique | |
| EP0376850B1 (fr) | Dérivés du benzène, leur préparation et compositions pharmaceutiques les contenant | |
| EP0348257A2 (fr) | Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique | |
| BE779775A (fr) | Derives de l'uree, procede pour les preparer et leurs applications | |
| BE569077A (fi) | ||
| CH638183A5 (fr) | Derives de pyrrolidine et de piperidine. | |
| EP0002401B1 (fr) | Dérivés de naphtalène, leur préparation et leur application en thérapeutique | |
| FR2560873A1 (fr) | Medicaments a base de derives de la piperidine, nouveaux derives de la piperidine et leurs procedes de preparation | |
| FR2628738A1 (fr) | Produits chimiques intermediaires utilisables pour la preparation de certains agents anti-histaminiques h2 | |
| BE569076A (fi) | ||
| EP0080419B1 (fr) | Haloalkyl-8-4H-(1)-benzopyran-4-ones, et procédés de préparation | |
| EP0228356B1 (fr) | Nouveaux dérivés d'hydroxy-4 indole, leur procédé de préparation et leur utilisation | |
| BE884977A (fr) | Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes | |
| BE569079A (fi) | ||
| FR2615853A1 (fr) | Nouveau procede pour la preparation de derives de la piperazine pharmacologiquement actifs, derives et nouveaux intermediaires obtenus | |
| BE706623A (fi) | ||
| BE569078A (fi) | ||
| BE568943A (fi) | ||
| BE590187A (fi) | ||
| CH627163A5 (en) | Processes for the preparation of new indole derivatives | |
| BE566396A (fi) | ||
| BE531615A (fi) | ||
| BE566395A (fi) | ||
| BE893872A (fr) | Derives d'ergoline |