DE2152742A1 - Verfahren zur Herstellung von 4-Aminopyrimidinen - Google Patents
Verfahren zur Herstellung von 4-AminopyrimidinenInfo
- Publication number
- DE2152742A1 DE2152742A1 DE19712152742 DE2152742A DE2152742A1 DE 2152742 A1 DE2152742 A1 DE 2152742A1 DE 19712152742 DE19712152742 DE 19712152742 DE 2152742 A DE2152742 A DE 2152742A DE 2152742 A1 DE2152742 A1 DE 2152742A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- methylpyrimidine
- ethyl
- mixture
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 150000005007 4-aminopyrimidines Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 aliphatic amidine Chemical class 0.000 claims description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- MKKZJLALSXXPJP-UHFFFAOYSA-N 2-ethyl-6-methylpyrimidin-4-amine Chemical compound CCC1=NC(C)=CC(N)=N1 MKKZJLALSXXPJP-UHFFFAOYSA-N 0.000 claims description 9
- BJJDXAFKCKSLTE-UHFFFAOYSA-N 2,6-dimethylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C)=N1 BJJDXAFKCKSLTE-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims description 6
- LAERIBHKDNBVOO-UHFFFAOYSA-N 6-methylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC=N1 LAERIBHKDNBVOO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RTYZKRMNFGEBAR-UHFFFAOYSA-N 2,6-diethyl-5-methylpyrimidin-4-amine Chemical compound CCC1=NC(N)=C(C)C(CC)=N1 RTYZKRMNFGEBAR-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 34
- 239000013078 crystal Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000002211 ultraviolet spectrum Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000012452 mother liquor Substances 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HTXJPHJQMHYRKJ-UHFFFAOYSA-N 2-ethyl-5-methylpyrimidin-4-amine Chemical compound CCC1=NC=C(C)C(N)=N1 HTXJPHJQMHYRKJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 2
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YMGUMRVGRGIJHJ-UHFFFAOYSA-N 2,4-diethyl-5-methylpyrimidine Chemical compound CCC1=NC=C(C)C(CC)=N1 YMGUMRVGRGIJHJ-UHFFFAOYSA-N 0.000 description 1
- FBEIDYLEFVIOEY-UHFFFAOYSA-N 2-chloro-6-methylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(Cl)=N1 FBEIDYLEFVIOEY-UHFFFAOYSA-N 0.000 description 1
- TVVBLCCMAVXQJK-UHFFFAOYSA-N 2-ethyl-5,6-dimethylpyrimidin-4-amine Chemical compound CCC1=NC(C)=C(C)C(N)=N1 TVVBLCCMAVXQJK-UHFFFAOYSA-N 0.000 description 1
- GKVDLTTVBNOGNJ-UHFFFAOYSA-N 2-methylpyrimidin-4-amine Chemical compound CC1=NC=CC(N)=N1 GKVDLTTVBNOGNJ-UHFFFAOYSA-N 0.000 description 1
- KFGLQUGZFWBETP-UHFFFAOYSA-N 4-amino-2-ethyl-6-methylpyrimidine-5-carbonitrile Chemical compound NC1=NC(=NC(=C1C#N)C)CC KFGLQUGZFWBETP-UHFFFAOYSA-N 0.000 description 1
- PVWNFAGYFUUDRC-UHFFFAOYSA-N 4-amino-5-formamidomethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CNC=O)C(N)=N1 PVWNFAGYFUUDRC-UHFFFAOYSA-N 0.000 description 1
- JGDLMVUAPKUNOH-UHFFFAOYSA-N 4-amino-6-ethyl-2-methylpyrimidine-5-carbonitrile Chemical compound CCC1=NC(C)=NC(N)=C1C#N JGDLMVUAPKUNOH-UHFFFAOYSA-N 0.000 description 1
- MVAXKFAQKTWRAH-UHFFFAOYSA-N 4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC=N1 MVAXKFAQKTWRAH-UHFFFAOYSA-N 0.000 description 1
- VBRADVACNORHOB-UHFFFAOYSA-N 4-ethyl-2,5-dimethylpyrimidine Chemical compound CCC1=NC(C)=NC=C1C VBRADVACNORHOB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- GOJDSMIXPMMHPO-UHFFFAOYSA-N n-propanoylpropanamide Chemical compound CCC(=O)NC(=O)CC GOJDSMIXPMMHPO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9295170A JPS5031157B1 (enrdf_load_stackoverflow) | 1970-10-22 | 1970-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152742A1 true DE2152742A1 (de) | 1972-04-27 |
Family
ID=14068756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152742 Pending DE2152742A1 (de) | 1970-10-22 | 1971-10-22 | Verfahren zur Herstellung von 4-Aminopyrimidinen |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5031157B1 (enrdf_load_stackoverflow) |
| CA (1) | CA949577A (enrdf_load_stackoverflow) |
| CH (1) | CH568300A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2152742A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2113059A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1329369A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384370A1 (de) * | 1989-02-22 | 1990-08-29 | Hoechst Aktiengesellschaft | Substituierte Pyrimidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Tool |
-
1970
- 1970-10-22 JP JP9295170A patent/JPS5031157B1/ja active Pending
-
1971
- 1971-10-04 CA CA124,275A patent/CA949577A/en not_active Expired
- 1971-10-18 GB GB4840971A patent/GB1329369A/en not_active Expired
- 1971-10-21 CH CH1531871A patent/CH568300A5/xx not_active IP Right Cessation
- 1971-10-21 FR FR7137857A patent/FR2113059A5/fr not_active Expired
- 1971-10-22 DE DE19712152742 patent/DE2152742A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384370A1 (de) * | 1989-02-22 | 1990-08-29 | Hoechst Aktiengesellschaft | Substituierte Pyrimidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Tool |
| US5138058A (en) * | 1989-02-22 | 1992-08-11 | Hoechst Aktiengesellschaft | Piperazine substituted pyrimidine derivatives and physiologically tolerated salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2113059A5 (enrdf_load_stackoverflow) | 1972-06-23 |
| CA949577A (en) | 1974-06-18 |
| CH568300A5 (enrdf_load_stackoverflow) | 1975-10-31 |
| JPS5031157B1 (enrdf_load_stackoverflow) | 1975-10-07 |
| GB1329369A (en) | 1973-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |