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 43
- 239000011780 sodium chloride Substances 0.000 claims description 23
- 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 18
- 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
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 12
- 150000002429 hydrazines Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
- 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 atoms Chemical group [H]* 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Carbodicyclohexylimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- FWWDFDMCZLOXQI-UHFFFAOYSA-N N'-benzyl-2,2-dimethylpropanehydrazide Chemical compound CC(C)(C)C(=O)NNCC1=CC=CC=C1 FWWDFDMCZLOXQI-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
- 229940095076 benzaldehyde Drugs 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical group C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 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
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 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
- IEMAUAQJNPHUBQ-UHFFFAOYSA-N N'-benzylcyclohexanecarbohydrazide Chemical compound C1CCCCC1C(=O)NNCC1=CC=CC=C1 IEMAUAQJNPHUBQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000001430 anti-depressive Effects 0.000 claims description 2
- 239000000935 antidepressant agent Substances 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
- KQNPFQTWMSNSAP-UHFFFAOYSA-N Isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 6
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 3
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229940005513 ANTIDEPRESSANTS Drugs 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical class CC(C)NN KJAQRHMKLVGSCG-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 acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- 238000007792 addition Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- OARJXUPBZNUYBG-UHFFFAOYSA-N 2,2-dimethylpropanehydrazide Chemical compound CC(C)(C)C(=O)NN OARJXUPBZNUYBG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 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
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CGWBFZCBNLMLDT-UHFFFAOYSA-N C1(CCC1)C(=O)NNC(C)C Chemical compound C1(CCC1)C(=O)NNC(C)C CGWBFZCBNLMLDT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 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
- 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
- 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
- 238000001704 evaporation Methods 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
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 2
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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 group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N 4-Ethylbenzaldehyde Chemical compound CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-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
- LLQGNFNOLKUJFN-UHFFFAOYSA-N C(C(C)C)(=O)NNCC Chemical compound C(C(C)C)(=O)NNCC LLQGNFNOLKUJFN-UHFFFAOYSA-N 0.000 description 1
- AFFCNKPXUVCCSV-UHFFFAOYSA-N C(C)C(C(=O)NN=C(C)C)CCCC Chemical compound C(C)C(C(=O)NN=C(C)C)CCCC AFFCNKPXUVCCSV-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
- MQHWOCDLCIPJNH-UHFFFAOYSA-N C1(CCC1)C(=O)NNCC1=CC=CC=C1 Chemical compound C1(CCC1)C(=O)NNCC1=CC=CC=C1 MQHWOCDLCIPJNH-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
- ADFXKUOMJKEIND-UHFFFAOYSA-N Dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N Iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- PMPVIKIVABFJJI-UHFFFAOYSA-N cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-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
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 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
- SMVBADCAMQOTOV-UHFFFAOYSA-N ethyl cyclobutanecarboxylate Chemical compound CCOC(=O)C1CCC1 SMVBADCAMQOTOV-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
- 238000005755 formation reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000003301 hydrolyzing 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
- 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
- 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
- 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
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