FI56387C - Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan - Google Patents
Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan Download PDFInfo
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- FI56387C FI56387C FI445/72A FI44572A FI56387C FI 56387 C FI56387 C FI 56387C FI 445/72 A FI445/72 A FI 445/72A FI 44572 A FI44572 A FI 44572A FI 56387 C FI56387 C FI 56387C
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- formula
- alk
- same
- chloroethyl
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- 150000001875 compounds Chemical class 0.000 claims description 70
- -1 β-chloroethyl group Chemical group 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000001506 immunosuppresive effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 2
- MIQVAKCNWBAWPC-UHFFFAOYSA-N 2h-1,3,2-oxazaphosphinine Chemical class O1PN=CC=C1 MIQVAKCNWBAWPC-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 137
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
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- 239000003921 oil Substances 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 34
- 239000000706 filtrate Substances 0.000 description 31
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- 238000000967 suction filtration Methods 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000001816 cooling Methods 0.000 description 13
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- SBMJSKYKTAAHAB-UHFFFAOYSA-N 2-chloro-3-(2-chloroethyl)-1,3,2$l^{5}-oxazaphosphinane 2-oxide Chemical compound ClCCN1CCCOP1(Cl)=O SBMJSKYKTAAHAB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- ZSZKJARKHWCBJK-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNP1(=O)OCCCN1CCCl ZSZKJARKHWCBJK-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- UBRSKPGONDTDNE-UHFFFAOYSA-N 3-(2-chloroethylamino)propan-1-ol;hydrochloride Chemical compound Cl.OCCCNCCCl UBRSKPGONDTDNE-UHFFFAOYSA-N 0.000 description 4
- 206010062016 Immunosuppression Diseases 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000003053 immunization Effects 0.000 description 4
- 238000002649 immunization Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- MLKQJVFHEUORBO-UHFFFAOYSA-M silver;methanesulfonate Chemical compound [Ag+].CS([O-])(=O)=O MLKQJVFHEUORBO-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 241000589562 Brucella Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
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- 230000028993 immune response Effects 0.000 description 3
- 229960001428 mercaptopurine Drugs 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- LDJYQUUXVWTUMZ-UHFFFAOYSA-N 3-[3-methylsulfonyloxypropyl-(2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl)amino]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCN(CCCOS(C)(=O)=O)P1(=O)NCCCO1 LDJYQUUXVWTUMZ-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 2
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- PWQOZRPSDQKNPW-UHFFFAOYSA-N pentane-1-sulfonyl chloride Chemical compound CCCCCS(Cl)(=O)=O PWQOZRPSDQKNPW-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65844—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a five-membered ring which may be condensed with another ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2107936 | 1971-02-19 | ||
| DE2107936A DE2107936C3 (de) | 1971-02-19 | 1971-02-19 | Alkylsulfonsäureester von 2-Oxo-13,2-oxazaphosphorinanen und diese enthaltende pharmazeutische Präparate |
| DE2201675 | 1972-01-14 | ||
| DE19722201675 DE2201675A1 (de) | 1972-01-14 | 1972-01-14 | Alkylsulfonsaeureester 1,3,2-oxazaphospha-cyclischer verbindungen, verfahren zu ihrer herstellung und pharmazeutische praeparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56387B FI56387B (fi) | 1979-09-28 |
| FI56387C true FI56387C (fi) | 1980-01-10 |
Family
ID=25760687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI445/72A FI56387C (fi) | 1971-02-19 | 1972-02-18 | Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3828090A (cs) |
| JP (1) | JPS5620317B1 (cs) |
| AR (1) | AR195863A1 (cs) |
| BE (1) | BE779516A (cs) |
| CA (1) | CA957696A (cs) |
| CH (3) | CH586230A5 (cs) |
| DD (1) | DD94812A5 (cs) |
| DK (1) | DK137013C (cs) |
| ES (1) | ES399910A1 (cs) |
| FI (1) | FI56387C (cs) |
| FR (1) | FR2125595B1 (cs) |
| HK (1) | HK11477A (cs) |
| HU (1) | HU169427B (cs) |
| IE (1) | IE36065B1 (cs) |
| LU (1) | LU64702A1 (cs) |
| MY (1) | MY7700155A (cs) |
| NL (1) | NL170287C (cs) |
| SE (1) | SE381464B (cs) |
| YU (3) | YU38772A (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910982A (en) * | 1971-02-19 | 1975-10-07 | Asta Werke Ag Chem Fab | Alkylsulfonic acid esters of 1,3,2-oxazaphospha-cyclic compounds |
| US4085128A (en) * | 1974-11-20 | 1978-04-18 | Shionogi & Co., Ltd. | Cyclic phosphamide derivatives |
| CN114965770B (zh) * | 2022-05-24 | 2023-03-28 | 江苏海洋大学 | 一种异环磷酰胺原料药中起始物料、杂质d、杂质f的检测方法 |
-
1972
- 1972-01-31 CH CH1183675A patent/CH586230A5/xx not_active IP Right Cessation
- 1972-01-31 CH CH134972A patent/CH581145A5/xx not_active IP Right Cessation
- 1972-01-31 CH CH1183575A patent/CH596231A5/xx not_active IP Right Cessation
- 1972-02-01 LU LU64702D patent/LU64702A1/xx unknown
- 1972-02-07 IE IE147/72A patent/IE36065B1/xx unknown
- 1972-02-10 US US00225273A patent/US3828090A/en not_active Expired - Lifetime
- 1972-02-16 YU YU00387/72A patent/YU38772A/xx unknown
- 1972-02-17 SE SE7201916A patent/SE381464B/xx unknown
- 1972-02-17 DD DD160930A patent/DD94812A5/xx unknown
- 1972-02-18 CA CA135,044A patent/CA957696A/en not_active Expired
- 1972-02-18 DK DK76172A patent/DK137013C/da not_active IP Right Cessation
- 1972-02-18 JP JP1655672A patent/JPS5620317B1/ja active Pending
- 1972-02-18 BE BE779516A patent/BE779516A/xx not_active IP Right Cessation
- 1972-02-18 NL NLAANVRAGE7202177,A patent/NL170287C/xx not_active IP Right Cessation
- 1972-02-18 AR AR240595A patent/AR195863A1/es active
- 1972-02-18 FI FI445/72A patent/FI56387C/fi active
- 1972-02-18 HU HUAA698A patent/HU169427B/hu unknown
- 1972-02-18 ES ES399910A patent/ES399910A1/es not_active Expired
- 1972-02-18 FR FR7205549A patent/FR2125595B1/fr not_active Expired
-
1977
- 1977-03-03 HK HK114/77A patent/HK11477A/xx unknown
- 1977-12-30 MY MY155/77A patent/MY7700155A/xx unknown
-
1978
- 1978-10-12 YU YU2388/78A patent/YU35030B/xx unknown
- 1978-10-12 YU YU2387/78A patent/YU35031B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL170287B (nl) | 1982-05-17 |
| FR2125595B1 (cs) | 1975-03-14 |
| AU3891472A (en) | 1973-08-16 |
| DD94812A5 (cs) | 1973-01-05 |
| AR195863A1 (es) | 1973-11-15 |
| LU64702A1 (cs) | 1972-06-29 |
| BE779516A (fr) | 1972-06-16 |
| MY7700155A (en) | 1977-12-31 |
| IE36065L (en) | 1972-08-19 |
| ES399910A1 (es) | 1975-06-16 |
| YU38772A (en) | 1982-02-28 |
| US3828090A (en) | 1974-08-06 |
| YU238878A (en) | 1979-12-31 |
| NL170287C (nl) | 1982-10-18 |
| NL7202177A (cs) | 1972-08-22 |
| YU35030B (en) | 1980-06-30 |
| CA957696A (en) | 1974-11-12 |
| CH586230A5 (cs) | 1977-03-31 |
| SE381464B (sv) | 1975-12-08 |
| CH596231A5 (cs) | 1978-03-15 |
| FI56387B (fi) | 1979-09-28 |
| FR2125595A1 (cs) | 1972-09-29 |
| DK137013C (da) | 1978-06-05 |
| YU238778A (en) | 1979-12-31 |
| YU35031B (en) | 1980-06-30 |
| HK11477A (en) | 1977-03-11 |
| IE36065B1 (en) | 1976-08-04 |
| CH581145A5 (cs) | 1976-10-29 |
| DK137013B (da) | 1978-01-02 |
| HU169427B (cs) | 1976-11-28 |
| JPS5620317B1 (cs) | 1981-05-13 |
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