SU471719A3 - Способ получени нитрофуриламиноалкоксипиримидина - Google Patents
Способ получени нитрофуриламиноалкоксипиримидинаInfo
- Publication number
- SU471719A3 SU471719A3 SU1453464A SU1453464A SU471719A3 SU 471719 A3 SU471719 A3 SU 471719A3 SU 1453464 A SU1453464 A SU 1453464A SU 1453464 A SU1453464 A SU 1453464A SU 471719 A3 SU471719 A3 SU 471719A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- furyl
- pyrimidine
- product
- yield
- ethoxy
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 26
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 25
- -1 halide hydrochloric acids Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 8
- NEFZJOPYDIFHHR-UHFFFAOYSA-N 5-(2-chloroethoxy)-2-(furan-2-yl)pyrimidine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCCl NEFZJOPYDIFHHR-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PZEZRQYIQIDRTR-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxy-N,N-dimethylethanamine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C)C PZEZRQYIQIDRTR-UHFFFAOYSA-N 0.000 description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OEMVQAXIIOBWBK-UHFFFAOYSA-N N,N-diethyl-2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethanamine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(CC)CC OEMVQAXIIOBWBK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical class CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- DIVVHXHYYGSKTC-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-5-(2-pyrrolidin-1-ylethoxy)pyrimidine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN1CCCC1 DIVVHXHYYGSKTC-UHFFFAOYSA-N 0.000 description 1
- ATCBZALBRYMBPF-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-5-(2-pyrrolidin-1-ylethoxy)pyrimidine sulfuric acid Chemical compound S(=O)(=O)(O)O.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN1CCCC1 ATCBZALBRYMBPF-UHFFFAOYSA-N 0.000 description 1
- JFXFXZTYAHPFNT-UHFFFAOYSA-N 2-(furan-2-yl)-5-(2-pyrrolidin-1-ylethoxy)pyrimidine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN1CCCC1 JFXFXZTYAHPFNT-UHFFFAOYSA-N 0.000 description 1
- JXYVGJBTUCSGHP-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethanol Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCO JXYVGJBTUCSGHP-UHFFFAOYSA-N 0.000 description 1
- XQQIGLPLFSRAJT-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl 4-methylbenzenesulfonate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCOS(=O)(=O)C1=CC=C(C=C1)C XQQIGLPLFSRAJT-UHFFFAOYSA-N 0.000 description 1
- AEXIQPQOFKQACC-UHFFFAOYSA-N 2-ethoxypyrimidine Chemical compound CCOC1=NC=CC=N1 AEXIQPQOFKQACC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- SMWPQXJOCORRRV-UHFFFAOYSA-N C1CCCN(CC1)CCOC2=CN=C(N=C2)C3=CC=C(O3)[N+](=O)[O-] Chemical compound C1CCCN(CC1)CCOC2=CN=C(N=C2)C3=CC=C(O3)[N+](=O)[O-] SMWPQXJOCORRRV-UHFFFAOYSA-N 0.000 description 1
- XYFIMOCIZVDOMG-UHFFFAOYSA-N Cl.O1C(=CC=C1)C1=NC=C(C=N1)OCCN(CCCC)CCCC Chemical compound Cl.O1C(=CC=C1)C1=NC=C(C=N1)OCCN(CCCC)CCCC XYFIMOCIZVDOMG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- QNFUPIJOMYJRLS-UHFFFAOYSA-N N,N-dimethyl-2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethanamine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C)C QNFUPIJOMYJRLS-UHFFFAOYSA-N 0.000 description 1
- VVMDYOAOZDPVRQ-UHFFFAOYSA-N N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]-N-propylpropan-1-amine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(CCC)CCC VVMDYOAOZDPVRQ-UHFFFAOYSA-N 0.000 description 1
- VZXWDYGMMFGEFJ-UHFFFAOYSA-N N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]-N-propylpropan-1-amine hydrochloride Chemical compound Cl.O1C(=CC=C1)C1=NC=C(C=N1)OCCN(CCC)CCC VZXWDYGMMFGEFJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
- C07D239/34—One oxygen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1937629A DE1937629C3 (de) | 1969-07-19 | 1969-07-19 | Nitrofuryl-aminoalkoxy-pyriinidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU471719A3 true SU471719A3 (ru) | 1975-05-25 |
Family
ID=5740764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1453464A SU471719A3 (ru) | 1969-07-19 | 1969-07-19 | Способ получени нитрофуриламиноалкоксипиримидина |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3707485A (enExample) |
| JP (1) | JPS4911236B1 (enExample) |
| AT (1) | AT294845B (enExample) |
| BE (1) | BE753632A (enExample) |
| CA (1) | CA929523A (enExample) |
| CH (1) | CH540927A (enExample) |
| CS (1) | CS166011B2 (enExample) |
| DE (1) | DE1937629C3 (enExample) |
| DK (1) | DK125097B (enExample) |
| ES (1) | ES381433A1 (enExample) |
| FR (1) | FR2059534B1 (enExample) |
| GB (1) | GB1320548A (enExample) |
| IL (1) | IL34882A (enExample) |
| NL (1) | NL7010681A (enExample) |
| NO (1) | NO127398B (enExample) |
| PL (1) | PL70032B1 (enExample) |
| SE (1) | SE367411B (enExample) |
| SU (1) | SU471719A3 (enExample) |
| ZA (1) | ZA704674B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2113529C3 (de) * | 1971-03-17 | 1980-04-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-(5-Nitro-2-furyl)-5-(2-alkylaminoäthoxy)-pyrimidin-Verbindungen |
| JPS5131086U (enExample) * | 1974-08-28 | 1976-03-06 | ||
| US4648896A (en) * | 1982-11-15 | 1987-03-10 | Ciba-Geigy Corporation | 2-aryl-4,6-dihalopyrimidines as antidote for protecting cultivated plants from phytotoxic damage caused by herbicides |
| CA2434972C (en) | 2001-01-16 | 2010-06-08 | Vascular Therapies, Llc | Implantable device containing resorbable matrix material and anti-proliferative drugs for preventing or treating failure of hemodialysis vascular access and other vascular grafts |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695849A1 (de) * | 1967-06-23 | 1971-05-13 | Schering Ag | Verfahren zur Herstellung neuer Pyrimidinderivate |
-
1969
- 1969-07-19 DE DE1937629A patent/DE1937629C3/de not_active Expired
- 1969-07-19 SU SU1453464A patent/SU471719A3/ru active
-
1970
- 1970-06-09 CH CH864570A patent/CH540927A/de not_active IP Right Cessation
- 1970-07-02 AT AT597970A patent/AT294845B/de not_active IP Right Cessation
- 1970-07-02 CS CS4622A patent/CS166011B2/cs unknown
- 1970-07-03 ES ES381433A patent/ES381433A1/es not_active Expired
- 1970-07-07 ZA ZA704674A patent/ZA704674B/xx unknown
- 1970-07-09 IL IL34882A patent/IL34882A/en unknown
- 1970-07-14 DK DK364970AA patent/DK125097B/da unknown
- 1970-07-15 GB GB3432270A patent/GB1320548A/en not_active Expired
- 1970-07-16 US US55601A patent/US3707485A/en not_active Expired - Lifetime
- 1970-07-16 CA CA088396A patent/CA929523A/en not_active Expired
- 1970-07-17 SE SE09942/70A patent/SE367411B/xx unknown
- 1970-07-17 BE BE753632D patent/BE753632A/xx unknown
- 1970-07-17 FR FR7026413A patent/FR2059534B1/fr not_active Expired
- 1970-07-17 NL NL7010681A patent/NL7010681A/xx unknown
- 1970-07-18 PL PL1970142152A patent/PL70032B1/pl unknown
- 1970-07-18 NO NO02825/70A patent/NO127398B/no unknown
- 1970-07-20 JP JP45063483A patent/JPS4911236B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL34882A (en) | 1972-10-29 |
| GB1320548A (en) | 1973-06-13 |
| DE1937629B2 (de) | 1978-11-16 |
| FR2059534A1 (enExample) | 1971-06-04 |
| NL7010681A (enExample) | 1971-01-21 |
| PL70032B1 (enExample) | 1973-12-31 |
| DK125097B (da) | 1972-12-27 |
| DE1937629C3 (de) | 1979-07-26 |
| US3707485A (en) | 1972-12-26 |
| ZA704674B (en) | 1971-03-31 |
| ES381433A1 (es) | 1972-12-01 |
| CS166011B2 (enExample) | 1976-01-29 |
| BE753632A (fr) | 1971-01-18 |
| JPS4911236B1 (enExample) | 1974-03-15 |
| DE1937629A1 (de) | 1971-02-11 |
| CA929523A (en) | 1973-07-03 |
| FR2059534B1 (enExample) | 1974-03-22 |
| NO127398B (enExample) | 1973-06-18 |
| AT294845B (de) | 1971-12-10 |
| SE367411B (enExample) | 1974-05-27 |
| CH540927A (de) | 1973-08-31 |
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