NO135591B - - Google Patents
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- Publication number
- NO135591B NO135591B NO2693/72A NO269372A NO135591B NO 135591 B NO135591 B NO 135591B NO 2693/72 A NO2693/72 A NO 2693/72A NO 269372 A NO269372 A NO 269372A NO 135591 B NO135591 B NO 135591B
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- alkyl
- nitrone
- substituted
- iminomethyl
- Prior art date
Links
- -1 alkoxyethyl nitrone Chemical compound 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 150000004959 2-nitroimidazoles Chemical class 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- PTQVJTGPPNNFIZ-UHFFFAOYSA-N n-cyclohexylmethanimine oxide Chemical compound [O-][N+](=C)C1CCCCC1 PTQVJTGPPNNFIZ-UHFFFAOYSA-N 0.000 claims description 2
- RQUUDWRETZBLHA-UHFFFAOYSA-N n-phenylmethanimine oxide Chemical compound [O-][N+](=C)C1=CC=CC=C1 RQUUDWRETZBLHA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PTLILCRCEWAQGA-UHFFFAOYSA-N 3-methyl-2-nitroimidazole-4-carbaldehyde Chemical compound CN1C(C=O)=CN=C1[N+]([O-])=O PTLILCRCEWAQGA-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- YGKXZPLRNQNOOC-UHFFFAOYSA-N 2-(2-amino-5-ethylimidazol-1-yl)ethanol;hydrochloride Chemical compound Cl.CCC1=CN=C(N)N1CCO YGKXZPLRNQNOOC-UHFFFAOYSA-N 0.000 description 1
- JYFTVKAMVHZXQD-UHFFFAOYSA-N 2-[2-[(3-methyl-2-nitroimidazol-4-yl)methylidene]hydrazinyl]ethanol Chemical compound CN1C(C=NNCCO)=CN=C1[N+]([O-])=O JYFTVKAMVHZXQD-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- IYHYEIBYGGWASC-UHFFFAOYSA-N 3-ethyl-2-nitroimidazole-4-carbaldehyde Chemical compound CCN1C(C=O)=CN=C1[N+]([O-])=O IYHYEIBYGGWASC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- AVXDZHRDHDWVGL-UHFFFAOYSA-N [(3-ethyl-2-nitroimidazol-4-yl)methylideneamino]thiourea Chemical compound CCN1C(C=NNC(N)=S)=CN=C1[N+]([O-])=O AVXDZHRDHDWVGL-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- MQNAOOIFODUDES-UHFFFAOYSA-N o-decylhydroxylamine Chemical compound CCCCCCCCCCON MQNAOOIFODUDES-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/91—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT4297871 | 1971-07-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135591B true NO135591B (fr) | 1977-01-17 |
| NO135591C NO135591C (fr) | 1977-04-27 |
Family
ID=11254772
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2693/72A NO135591C (fr) | 1971-07-30 | 1972-07-27 | |
| NO2694/72A NO135592C (fr) | 1971-07-30 | 1972-07-27 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2694/72A NO135592C (fr) | 1971-07-30 | 1972-07-27 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3954789A (fr) |
| JP (2) | JPS5038111B1 (fr) |
| AR (4) | AR193885A1 (fr) |
| AT (3) | AT315164B (fr) |
| AU (1) | AU462723B2 (fr) |
| BE (1) | BE785024A (fr) |
| CA (1) | CA997340A (fr) |
| CH (4) | CH572040A5 (fr) |
| CS (1) | CS180585B2 (fr) |
| DD (2) | DD99995A5 (fr) |
| DE (2) | DE2229248C3 (fr) |
| DK (1) | DK154295C (fr) |
| ES (3) | ES405341A1 (fr) |
| FI (1) | FI57255C (fr) |
| FR (1) | FR2148073B1 (fr) |
| GB (1) | GB1362444A (fr) |
| HU (2) | HU167622B (fr) |
| IE (1) | IE36530B1 (fr) |
| IL (1) | IL39880A (fr) |
| LU (1) | LU65816A1 (fr) |
| NL (2) | NL149491B (fr) |
| NO (2) | NO135591C (fr) |
| PL (4) | PL85190B1 (fr) |
| RO (6) | RO62787A (fr) |
| SE (3) | SE417711B (fr) |
| SU (4) | SU463263A3 (fr) |
| ZA (1) | ZA724723B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1480192A (en) * | 1975-01-15 | 1977-07-20 | Lepetit Spa | 1-methyl-2-nitro-imidazole-5-methanol derivatives |
| GB1526451A (en) * | 1976-01-27 | 1978-09-27 | Lepetit Spa | Alpha,alpha,1-trimethyl-2-nitroimidazole-5-methanol derivatives |
| US4218460A (en) * | 1976-09-29 | 1980-08-19 | Basf Aktiengesellschaft | Nitroimidazoles |
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| ZW24982A1 (en) * | 1981-11-30 | 1983-06-15 | Hoffmann La Roche | 2-nitroimidazoles |
| JPH10338673A (ja) * | 1997-06-04 | 1998-12-22 | Nippon Bayeragrochem Kk | イソニコチン酸ヒドラジド誘導体および有害生物防除剤 |
| ZA200507752B (en) | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
| NZ565378A (en) | 2005-06-29 | 2011-03-31 | Threshold Pharmaceuticals Inc | Phosphoramidate alkylator prodrugs |
| JP5357049B2 (ja) | 2006-12-26 | 2013-12-04 | スレッシュオールド ファーマシューティカルズ， インコーポレイテッド | 癌の治療のためのフォスフォルアミデートアルキル化剤プロドラッグ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL124627C (fr) * | 1964-08-12 | |||
| NL143227B (nl) * | 1968-11-15 | 1974-09-16 | Lepetit Spa | Werkwijze ter bereiding van imidazoolderivaten met bactericide werking. |
| US3583985A (en) * | 1969-04-09 | 1971-06-08 | Richardson Merrell Inc | Nitroimidazolyl nitrones |
| US3711495A (en) * | 1970-01-07 | 1973-01-16 | Merck & Co Inc | Isoxazalin-3-yl-substituted-5-nitroimidazoles |
-
1972
- 1972-06-15 DE DE2229248A patent/DE2229248C3/de not_active Expired
- 1972-06-15 DE DE2229223A patent/DE2229223C3/de not_active Expired
- 1972-06-16 BE BE785024A patent/BE785024A/fr not_active IP Right Cessation
- 1972-06-30 FI FI1864/72A patent/FI57255C/fi active
- 1972-07-05 IE IE944/72A patent/IE36530B1/xx unknown
- 1972-07-05 AU AU44228/72A patent/AU462723B2/en not_active Expired
- 1972-07-11 IL IL39880A patent/IL39880A/en unknown
- 1972-07-11 ZA ZA724723A patent/ZA724723B/xx unknown
- 1972-07-13 GB GB3288672A patent/GB1362444A/en not_active Expired
- 1972-07-20 AR AR243171A patent/AR193885A1/es active
- 1972-07-20 AR AR243172A patent/AR199084A1/es active
- 1972-07-20 AR AR243170A patent/AR193999A1/es active
- 1972-07-25 SU SU1812191A patent/SU463263A3/ru active
- 1972-07-25 SU SU1812193A patent/SU466684A3/ru active
- 1972-07-26 DK DK369072A patent/DK154295C/da not_active IP Right Cessation
- 1972-07-26 US US05/275,415 patent/US3954789A/en not_active Expired - Lifetime
- 1972-07-27 CS CS7200005305A patent/CS180585B2/cs unknown
- 1972-07-27 NO NO2693/72A patent/NO135591C/no unknown
- 1972-07-27 JP JP47075507A patent/JPS5038111B1/ja active Pending
- 1972-07-27 NO NO2694/72A patent/NO135592C/no unknown
- 1972-07-27 JP JP47075508A patent/JPS528832B1/ja active Pending
- 1972-07-27 NL NL727210340A patent/NL149491B/xx not_active IP Right Cessation
- 1972-07-27 NL NL727210339A patent/NL148602B/xx not_active IP Right Cessation
- 1972-07-28 HU HULE663A patent/HU167622B/hu unknown
- 1972-07-28 SE SE7209897A patent/SE417711B/xx unknown
- 1972-07-28 RO RO71769A patent/RO62787A/ro unknown
- 1972-07-28 LU LU65816D patent/LU65816A1/xx unknown
- 1972-07-28 CH CH1127772A patent/CH572040A5/xx not_active IP Right Cessation
- 1972-07-28 PL PL1972156989A patent/PL85190B1/pl unknown
- 1972-07-28 FR FR7227293A patent/FR2148073B1/fr not_active Expired
- 1972-07-28 CH CH1521175A patent/CH574934A5/xx not_active IP Right Cessation
- 1972-07-28 AT AT652872A patent/AT315164B/de not_active IP Right Cessation
- 1972-07-28 RO RO7200079769A patent/RO63047A/fr unknown
- 1972-07-28 DD DD164754A patent/DD99995A5/xx unknown
- 1972-07-28 SE SE7209898A patent/SE392615B/xx unknown
- 1972-07-28 AT AT686873A patent/AT323736B/de not_active IP Right Cessation
- 1972-07-28 PL PL1972175045A patent/PL84350B1/pl unknown
- 1972-07-28 PL PL1972156990A patent/PL82980B1/pl unknown
- 1972-07-28 PL PL1972163819A patent/PL87673B1/pl unknown
- 1972-07-28 RO RO7200075751A patent/RO63453A/fr unknown
- 1972-07-28 DD DD164752A patent/DD99996A5/xx unknown
- 1972-07-28 RO RO7200079770A patent/RO63048A/fr unknown
- 1972-07-28 HU HULE664A patent/HU164926B/hu unknown
- 1972-07-28 CH CH1521075A patent/CH574933A5/xx not_active IP Right Cessation
- 1972-07-28 AT AT652772A patent/AT316545B/de not_active IP Right Cessation
- 1972-07-28 RO RO71770A patent/RO61517A/ro unknown
- 1972-07-28 CH CH1127672A patent/CH580596A5/xx not_active IP Right Cessation
- 1972-07-28 RO RO7200079771A patent/RO63049A/fr unknown
- 1972-07-29 ES ES405341A patent/ES405341A1/es not_active Expired
- 1972-07-29 ES ES405343A patent/ES405343A1/es not_active Expired
- 1972-07-31 CA CA148,336A patent/CA997340A/en not_active Expired
-
1973
- 1973-06-27 SU SU7301932092A patent/SU581863A3/ru active
- 1973-08-02 AR AR249413A patent/AR199680A1/es active
- 1973-09-20 ES ES418921A patent/ES418921A1/es not_active Expired
- 1973-12-24 SU SU7301978810A patent/SU567404A3/ru active
-
1975
- 1975-03-18 SE SE7503080A patent/SE417200B/xx not_active IP Right Cessation
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