GB607720A - Manufacture of biguanide derivatives - Google Patents
Manufacture of biguanide derivativesInfo
- Publication number
- GB607720A GB607720A GB35238/45A GB3523845A GB607720A GB 607720 A GB607720 A GB 607720A GB 35238/45 A GB35238/45 A GB 35238/45A GB 3523845 A GB3523845 A GB 3523845A GB 607720 A GB607720 A GB 607720A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- methyl
- iodo
- bromo
- phenyl
- 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.)
- Expired
Links
- 150000004283 biguanides Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000011734 sodium Substances 0.000 abstract 28
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 12
- 239000000243 solution Substances 0.000 abstract 9
- 150000003839 salts Chemical class 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 4
- -1 acetic Chemical class 0.000 abstract 4
- 150000002357 guanidines Chemical class 0.000 abstract 4
- GKFFFNUVYUGXEW-UHFFFAOYSA-N (4-chlorophenyl)cyanamide Chemical compound ClC1=CC=C(NC#N)C=C1 GKFFFNUVYUGXEW-UHFFFAOYSA-N 0.000 abstract 3
- ZSJNJAJDBNFVCA-UHFFFAOYSA-N 2-(4-chlorophenyl)guanidine Chemical compound NC(=N)NC1=CC=C(Cl)C=C1 ZSJNJAJDBNFVCA-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- QIRSDXBXWUTMRE-UHFFFAOYSA-N benzylcyanamide Chemical compound N#CNCC1=CC=CC=C1 QIRSDXBXWUTMRE-UHFFFAOYSA-N 0.000 abstract 3
- 150000001912 cyanamides Chemical class 0.000 abstract 3
- ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 229940123208 Biguanide Drugs 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- GYEOFMXQZPOQIX-UHFFFAOYSA-N propan-2-ylcyanamide Chemical compound CC(C)NC#N GYEOFMXQZPOQIX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- INKUFJVBSFNXFI-UHFFFAOYSA-N (3-bromophenyl)cyanamide Chemical compound BrC1=CC=CC(NC#N)=C1 INKUFJVBSFNXFI-UHFFFAOYSA-N 0.000 abstract 1
- XCCLGXDHWKXYNS-UHFFFAOYSA-N (3-methylphenyl)cyanamide Chemical compound CC1=CC=CC(NC#N)=C1 XCCLGXDHWKXYNS-UHFFFAOYSA-N 0.000 abstract 1
- FJUGLINMEXQSBP-UHFFFAOYSA-N (4-ethoxyphenyl)cyanamide Chemical compound CCOC1=CC=C(NC#N)C=C1 FJUGLINMEXQSBP-UHFFFAOYSA-N 0.000 abstract 1
- SGNLZDSZLBOVGT-UHFFFAOYSA-N (n'-benzylcarbamimidoyl)azanium;chloride Chemical compound [Cl-].[NH3+]C(=N)NCC1=CC=CC=C1 SGNLZDSZLBOVGT-UHFFFAOYSA-N 0.000 abstract 1
- VIEXAFPVDSRNAY-UHFFFAOYSA-N 1,2-dimethylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CNC(N)=NC VIEXAFPVDSRNAY-UHFFFAOYSA-N 0.000 abstract 1
- PNJBPUKZUWSJEJ-UHFFFAOYSA-N 1-butyl-1-methylguanidine Chemical compound CCCCN(C)C(N)=N PNJBPUKZUWSJEJ-UHFFFAOYSA-N 0.000 abstract 1
- AEKXWVSPVCTOIA-UHFFFAOYSA-N 1-methyl-1-propan-2-ylguanidine Chemical compound CC(C)N(C)C(N)=N AEKXWVSPVCTOIA-UHFFFAOYSA-N 0.000 abstract 1
- HKOZDRYXZCSING-UHFFFAOYSA-N 1-methyl-1-propylguanidine Chemical compound CCCN(C)C(N)=N HKOZDRYXZCSING-UHFFFAOYSA-N 0.000 abstract 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 abstract 1
- AQWZJHJPPCQCKV-UHFFFAOYSA-N 2-(3-bromo-4-chlorophenyl)guanidine Chemical compound NC(=N)NC1=CC=C(Cl)C(Br)=C1 AQWZJHJPPCQCKV-UHFFFAOYSA-N 0.000 abstract 1
- RMFZXBDENVVLSL-UHFFFAOYSA-N 2-(4-chlorophenyl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC1=CC=C(Cl)C=C1 RMFZXBDENVVLSL-UHFFFAOYSA-N 0.000 abstract 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 abstract 1
- AJGAPBXTFUSKNJ-UHFFFAOYSA-N 2-cyclohexylguanidine Chemical compound NC(=N)NC1CCCCC1 AJGAPBXTFUSKNJ-UHFFFAOYSA-N 0.000 abstract 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 abstract 1
- XMIWFFMIJCOJLR-UHFFFAOYSA-N 2-propan-2-ylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)N=C(N)N XMIWFFMIJCOJLR-UHFFFAOYSA-N 0.000 abstract 1
- BWMDMTSNSXYYSP-UHFFFAOYSA-N 2-propylguanidine Chemical compound CCCNC(N)=N BWMDMTSNSXYYSP-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- OQUUVTMCNHHOQE-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC#N.[Na] Chemical compound ClC1=CC=C(C=C1)NC#N.[Na] OQUUVTMCNHHOQE-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NXXNZLIDCGLOJK-UHFFFAOYSA-N O.BrC1=CC=C(C=C1)NC(=N)N Chemical compound O.BrC1=CC=C(C=C1)NC(=N)N NXXNZLIDCGLOJK-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- PQZVCRPSQXDXJL-UHFFFAOYSA-N butylcyanamide Chemical compound CCCCNC#N PQZVCRPSQXDXJL-UHFFFAOYSA-N 0.000 abstract 1
- XDSYAIICRRZSJX-UHFFFAOYSA-N carbamimidoyl(phenyl)azanium;hydrogen carbonate Chemical compound OC(O)=O.NC(N)=NC1=CC=CC=C1 XDSYAIICRRZSJX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- SOGFATPCYLMCMQ-UHFFFAOYSA-N dibutylcyanamide Chemical compound CCCCN(C#N)CCCC SOGFATPCYLMCMQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 abstract 1
- HHEBKNOWWBMJOL-UHFFFAOYSA-N methyl(propan-2-yl)cyanamide Chemical compound CC(C)N(C)C#N HHEBKNOWWBMJOL-UHFFFAOYSA-N 0.000 abstract 1
- RMFIGLFPQLPETG-UHFFFAOYSA-N methyl(propyl)cyanamide Chemical compound CCCN(C)C#N RMFIGLFPQLPETG-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- WGWKNMLSVLOQJB-UHFFFAOYSA-N propan-2-ylazanium;bromide Chemical compound Br.CC(C)N WGWKNMLSVLOQJB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35238/45A GB607720A (en) | 1945-12-31 | 1945-12-31 | Manufacture of biguanide derivatives |
| ES176286A ES176286A1 (es) | 1945-12-31 | 1946-12-31 | Un procedimiento para la obtención de derivados de biguanida |
| FR954888D FR954888A (enrdf_load_stackoverflow) | 1945-12-31 | 1946-12-31 | |
| FR58093D FR58093E (fr) | 1945-12-31 | 1948-03-15 | Procédé de fabrication de dérivés de la biguanide |
| CY7549A CY75A (en) | 1945-12-31 | 1949-02-04 | Manufacture of biguanide derivatives |
| MY12/54A MY5400012A (en) | 1945-12-31 | 1954-12-30 | Manufacture of biguanide derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35238/45A GB607720A (en) | 1945-12-31 | 1945-12-31 | Manufacture of biguanide derivatives |
| FR58093T | 1948-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB607720A true GB607720A (en) | 1948-09-03 |
Family
ID=61024212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35238/45A Expired GB607720A (en) | 1945-12-31 | 1945-12-31 | Manufacture of biguanide derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CY (1) | CY75A (enrdf_load_stackoverflow) |
| FR (2) | FR954888A (enrdf_load_stackoverflow) |
| GB (1) | GB607720A (enrdf_load_stackoverflow) |
| MY (1) | MY5400012A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529992A (en) * | 1948-02-20 | 1950-11-14 | Usines Chimiques Rhone Poulene | Production of n'-p-chlorophenyl-n-isopropyl biguanide |
| US2556315A (en) * | 1948-02-20 | 1951-06-12 | Rhone Poulenc Sa | Production of a salt of p-chlorophenyl cyanamide and isopropylguanidine |
| US2606923A (en) * | 1950-05-13 | 1952-08-12 | Rohm & Haas | Tertiary alkylcyanamides |
| WO2010132982A1 (en) * | 2009-05-18 | 2010-11-25 | Ottawa Hospital Research Institute | Treatment of muscle disease characterized by insulin resistance |
| EP2522653A4 (en) * | 2010-01-06 | 2013-06-12 | Hanall Biopharma Co Ltd | BIGUANIDE DERIVATIVE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE BIGUANIDE DERIVATIVE AS AN ACTIVE SUBSTANCE |
| US10626085B2 (en) | 2014-11-20 | 2020-04-21 | Immunomet Therapeutics Inc. | Biguanide compound and use thereof |
-
1945
- 1945-12-31 GB GB35238/45A patent/GB607720A/en not_active Expired
-
1946
- 1946-12-31 FR FR954888D patent/FR954888A/fr not_active Expired
-
1948
- 1948-03-15 FR FR58093D patent/FR58093E/fr not_active Expired
-
1949
- 1949-02-04 CY CY7549A patent/CY75A/xx unknown
-
1954
- 1954-12-30 MY MY12/54A patent/MY5400012A/xx unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529992A (en) * | 1948-02-20 | 1950-11-14 | Usines Chimiques Rhone Poulene | Production of n'-p-chlorophenyl-n-isopropyl biguanide |
| US2556315A (en) * | 1948-02-20 | 1951-06-12 | Rhone Poulenc Sa | Production of a salt of p-chlorophenyl cyanamide and isopropylguanidine |
| US2606923A (en) * | 1950-05-13 | 1952-08-12 | Rohm & Haas | Tertiary alkylcyanamides |
| WO2010132982A1 (en) * | 2009-05-18 | 2010-11-25 | Ottawa Hospital Research Institute | Treatment of muscle disease characterized by insulin resistance |
| US8993633B2 (en) | 2009-05-18 | 2015-03-31 | Fate Therapeutics, (Canada) Inc. | Treatment of muscle disease characterized by insulin resistance |
| EP2522653A4 (en) * | 2010-01-06 | 2013-06-12 | Hanall Biopharma Co Ltd | BIGUANIDE DERIVATIVE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE BIGUANIDE DERIVATIVE AS AN ACTIVE SUBSTANCE |
| US9416098B2 (en) | 2010-01-06 | 2016-08-16 | Immunomet Therapeutics Inc. | Biguanide derivative, a preparation method thereof and a pharmaceutical composition containing the biguanide derivative as an active ingredient |
| US9993446B2 (en) | 2010-01-06 | 2018-06-12 | Immunomet Therapeutics Inc. | Biguanide derivative, a preparation method thereof, and a pharmaceutical composition containing the biguanide derivative as an active ingredient |
| US10376480B2 (en) | 2010-01-06 | 2019-08-13 | Immunomet Therapeutics Inc. | Biguanide derivative, a preparation method thereof, and a pharmaceutical composition containing the biguanide derivative as an active ingredient |
| US10626085B2 (en) | 2014-11-20 | 2020-04-21 | Immunomet Therapeutics Inc. | Biguanide compound and use thereof |
| US11572341B2 (en) | 2014-11-20 | 2023-02-07 | Immunomet Therapeutics Inc. | Biguanide compound and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR954888A (enrdf_load_stackoverflow) | 1950-01-06 |
| FR58093E (fr) | 1953-09-21 |
| MY5400012A (en) | 1954-12-31 |
| CY75A (en) | 1949-02-04 |
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