IL24097A - The N-oxide-3-amino-pyrazinoic acid compounds and their esters, amides and hydrazides, and processes for their production - Google Patents
The N-oxide-3-amino-pyrazinoic acid compounds and their esters, amides and hydrazides, and processes for their productionInfo
- Publication number
- IL24097A IL24097A IL2409765A IL2409765A IL24097A IL 24097 A IL24097 A IL 24097A IL 2409765 A IL2409765 A IL 2409765A IL 2409765 A IL2409765 A IL 2409765A IL 24097 A IL24097 A IL 24097A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- formula
- reacted
- preparation
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 20
- 150000002148 esters Chemical class 0.000 title description 12
- 150000001408 amides Chemical class 0.000 title description 3
- ZAGZIOYVEIDDJA-UHFFFAOYSA-N 3-aminopyrazine-2-carboxylic acid Chemical compound NC1=NC=CN=C1C(O)=O ZAGZIOYVEIDDJA-UHFFFAOYSA-N 0.000 title description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 41
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical class OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229960005206 pyrazinamide Drugs 0.000 claims description 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- YHPMRHPLAQSPHJ-UHFFFAOYSA-N 3-chloropyrazine-2-carboxamide Chemical compound NC(=O)C1=NC=CN=C1Cl YHPMRHPLAQSPHJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- -1 pyrazinamide compound Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000007787 solid Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CIZZUEUKGNBQPP-UHFFFAOYSA-N ethyl 2-anilino-7-oxo-8-phenylpteridine-6-carboxylate Chemical compound N1=C2N(C=3C=CC=CC=3)C(=O)C(C(=O)OCC)=NC2=CN=C1NC1=CC=CC=C1 CIZZUEUKGNBQPP-UHFFFAOYSA-N 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VWXIHLCLIOQWRA-UHFFFAOYSA-N 1h-pteridin-2-one Chemical class N1=CC=NC2=NC(O)=NC=C21 VWXIHLCLIOQWRA-UHFFFAOYSA-N 0.000 description 1
- JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- XHQFBKFXVAFWIU-UHFFFAOYSA-N 2-sulfanylidene-1h-pyrazine-3-carboxylic acid Chemical compound OC(=O)C1=NC=CN=C1S XHQFBKFXVAFWIU-UHFFFAOYSA-N 0.000 description 1
- NSMRHYDOKZAMKJ-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one Chemical compound C1CCCC2=C1C1=CC=C(OP(=S)(OCC)OCC)C=C1OC2=O NSMRHYDOKZAMKJ-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- BEOAYHGWRUBNCB-UHFFFAOYSA-N [Na].O=c1ncc2nccnc2[nH]1 Chemical compound [Na].O=c1ncc2nccnc2[nH]1 BEOAYHGWRUBNCB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 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
- 229940125851 compound 27 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- TWIIRMSFZNYMQE-UHFFFAOYSA-N methyl pyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=CC=N1 TWIIRMSFZNYMQE-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US395046A US3249610A (en) | 1964-09-08 | 1964-09-08 | Synthesis of 3-amino, 5-chloro, 6-substituted-pyrazinoates |
| US426203A US3327287A (en) | 1965-01-18 | 1965-01-18 | Apparatus for converting lineal seismogram sections into an areally presented seismogram |
| US47035065A | 1965-07-08 | 1965-07-08 | |
| US47056365A | 1965-07-08 | 1965-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24097A true IL24097A (en) | 1969-11-12 |
Family
ID=27503371
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2409765A IL24097A (en) | 1964-09-08 | 1965-08-06 | The N-oxide-3-amino-pyrazinoic acid compounds and their esters, amides and hydrazides, and processes for their production |
| IL2409865A IL24098A (en) | 1964-09-08 | 1965-08-06 | Process for preparing 5-chloro-3-aminopyrazinoates |
| IL3178765A IL31787A (en) | 1964-09-08 | 1965-08-06 | 2-r5-4h-pyrazino(2,3-d)(1,3)-oxazin-4-one 8-oxides and processes for their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2409865A IL24098A (en) | 1964-09-08 | 1965-08-06 | Process for preparing 5-chloro-3-aminopyrazinoates |
| IL3178765A IL31787A (en) | 1964-09-08 | 1965-08-06 | 2-r5-4h-pyrazino(2,3-d)(1,3)-oxazin-4-one 8-oxides and processes for their preparation |
Country Status (8)
| Country | Link |
|---|---|
| BE (2) | BE668495A (de) |
| BR (3) | BR6572741D0 (de) |
| CH (3) | CH467271A (de) |
| DE (3) | DE1595953A1 (de) |
| GB (5) | GB1112724A (de) |
| IL (3) | IL24097A (de) |
| NL (3) | NL6511644A (de) |
| SE (1) | SE329629B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113200985B (zh) * | 2021-05-18 | 2022-09-09 | 南开大学 | 一种蝶啶酮类化合物及其制备方法和应用 |
| CN117946013B (zh) * | 2024-01-25 | 2024-07-02 | 白银康寓信生物科技有限公司 | 一锅法合成5,6-二卤代-3-氨基吡嗪-2-甲酸甲酯的方法 |
-
1965
- 1965-08-06 IL IL2409765A patent/IL24097A/en unknown
- 1965-08-06 IL IL2409865A patent/IL24098A/xx unknown
- 1965-08-06 IL IL3178765A patent/IL31787A/xx unknown
- 1965-08-19 BE BE668495D patent/BE668495A/xx unknown
- 1965-08-19 BE BE668496D patent/BE668496A/xx unknown
- 1965-08-24 DE DE19651595953 patent/DE1595953A1/de active Pending
- 1965-08-24 DE DE19651595952 patent/DE1595952A1/de active Pending
- 1965-08-31 BR BR17274165A patent/BR6572741D0/pt unknown
- 1965-08-31 BR BR17276965A patent/BR6572769D0/pt unknown
- 1965-09-07 GB GB3179467A patent/GB1112724A/en not_active Expired
- 1965-09-07 CH CH1243565A patent/CH467271A/de unknown
- 1965-09-07 GB GB3179365D patent/GB1112723A/en not_active Expired
- 1965-09-07 CH CH1075068A patent/CH466293A/de unknown
- 1965-09-07 GB GB3816765A patent/GB1112722A/en not_active Expired
- 1965-09-07 GB GB3816665A patent/GB1112721A/en not_active Expired
- 1965-09-07 NL NL6511644A patent/NL6511644A/xx unknown
- 1965-09-07 CH CH1243465A patent/CH475262A/de not_active IP Right Cessation
- 1965-09-07 SE SE1164765A patent/SE329629B/xx unknown
- 1965-09-07 NL NL6511643A patent/NL6511643A/xx unknown
-
1966
- 1966-06-07 DE DE19661620020 patent/DE1620020A1/de active Pending
- 1966-06-29 GB GB2907666A patent/GB1115406A/en not_active Expired
- 1966-07-06 BR BR18106066A patent/BR6681060D0/pt unknown
- 1966-07-08 NL NL6609629A patent/NL6609629A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1112723A (en) | 1968-05-08 |
| IL24098A (en) | 1969-03-27 |
| IL31787A (en) | 1969-07-30 |
| BE668495A (de) | 1966-02-21 |
| DE1620020A1 (de) | 1970-02-12 |
| GB1112722A (en) | 1968-05-08 |
| CH467271A (de) | 1969-01-15 |
| BE668496A (de) | 1966-02-21 |
| NL6511643A (de) | 1966-03-09 |
| BR6572769D0 (pt) | 1973-12-26 |
| GB1112721A (en) | 1968-05-08 |
| CH466293A (de) | 1968-12-15 |
| BR6681060D0 (pt) | 1973-12-26 |
| GB1112724A (en) | 1968-05-08 |
| BR6572741D0 (pt) | 1973-08-07 |
| GB1115406A (en) | 1968-05-29 |
| NL6511644A (de) | 1966-03-09 |
| NL6609629A (de) | 1967-01-09 |
| SE329629B (de) | 1970-10-19 |
| DE1595952A1 (de) | 1970-05-14 |
| DE1595953A1 (de) | 1970-07-09 |
| CH475262A (de) | 1969-07-15 |
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