FI57596C - Foerfarande foer framstaellning av 3',4'-dideoxikanamycin b som aer antibakteriell och speciellt aktiv mot infektioner orsakade av kanamycinresistenta organismer - Google Patents
Foerfarande foer framstaellning av 3',4'-dideoxikanamycin b som aer antibakteriell och speciellt aktiv mot infektioner orsakade av kanamycinresistenta organismer Download PDFInfo
- Publication number
- FI57596C FI57596C FI1744/71A FI174471A FI57596C FI 57596 C FI57596 C FI 57596C FI 1744/71 A FI1744/71 A FI 1744/71A FI 174471 A FI174471 A FI 174471A FI 57596 C FI57596 C FI 57596C
- Authority
- FI
- Finland
- Prior art keywords
- kanamycin
- antibacterial
- organism
- dideoxycanamycin
- ch2nh2
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 229960000318 kanamycin Drugs 0.000 claims description 10
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 10
- 229930182823 kanamycin A Natural products 0.000 claims description 10
- 229930027917 kanamycin Natural products 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
- XPIJMQVLTXAGME-UHFFFAOYSA-N 1,1-dimethoxycyclohexane Chemical compound COC1(OC)CCCCC1 XPIJMQVLTXAGME-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 description 19
- 229960001192 bekanamycin Drugs 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 229930182824 kanamycin B Natural products 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VSWICNJIUPRZIK-YFVHKJHSSA-N 1,2,2,3,3,4-hexadeuterio-4H-pyridine Chemical compound N1(C(C(C(C=C1)[2H])([2H])[2H])([2H])[2H])[2H] VSWICNJIUPRZIK-YFVHKJHSSA-N 0.000 description 3
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000295644 Staphylococcaceae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- JJCQSGDBDPYCEO-XVZSLQNASA-N dibekacin Chemical compound O1[C@H](CN)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N JJCQSGDBDPYCEO-XVZSLQNASA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 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 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6576070 | 1970-07-29 | ||
| JP45065760A JPS507595B1 (en, 2012) | 1970-07-29 | 1970-07-29 | |
| JP3087171 | 1971-05-11 | ||
| JP46030871A JPS5146110B1 (en, 2012) | 1971-05-11 | 1971-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57596B FI57596B (fi) | 1980-05-30 |
| FI57596C true FI57596C (fi) | 1980-09-10 |
Family
ID=26369303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1744/71A FI57596C (fi) | 1970-07-29 | 1971-06-18 | Foerfarande foer framstaellning av 3',4'-dideoxikanamycin b som aer antibakteriell och speciellt aktiv mot infektioner orsakade av kanamycinresistenta organismer |
Country Status (23)
| Country | Link |
|---|---|
| AT (1) | AT320846B (en, 2012) |
| BE (1) | BE770692A (en, 2012) |
| BG (1) | BG19188A3 (en, 2012) |
| CA (1) | CA953294A (en, 2012) |
| CH (1) | CH552586A (en, 2012) |
| DK (1) | DK127778B (en, 2012) |
| ES (1) | ES392570A1 (en, 2012) |
| FI (1) | FI57596C (en, 2012) |
| FR (1) | FR2103935A5 (en, 2012) |
| GB (1) | GB1349302A (en, 2012) |
| HK (1) | HK57477A (en, 2012) |
| HU (1) | HU162704B (en, 2012) |
| IE (1) | IE35480B1 (en, 2012) |
| IL (1) | IL36973A (en, 2012) |
| LU (1) | LU63625A1 (en, 2012) |
| MY (1) | MY7800147A (en, 2012) |
| NL (1) | NL163219C (en, 2012) |
| NO (1) | NO134117C (en, 2012) |
| PL (1) | PL83206B1 (en, 2012) |
| RO (1) | RO63815A (en, 2012) |
| SE (1) | SE398753B (en, 2012) |
| SU (1) | SU511007A3 (en, 2012) |
| YU (1) | YU35895B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1537905A (en) * | 1975-12-09 | 1979-01-10 | Microbial Chem Res Found | Processes for the preparation of 3',4'-dideoxykanamycin b |
| JPS6029720B2 (ja) * | 1975-12-11 | 1985-07-12 | 財団法人微生物化学研究会 | ３′，４′‐ジデオキシカナマイシンｂの新規な製造法 |
| JPS52153942A (en) * | 1976-06-16 | 1977-12-21 | Microbial Chem Res Found | Preparation of kanamicin c deoxy derivatives and kanamicine c or its deoxy derivatives |
| HU177398B (en) * | 1976-12-16 | 1981-12-28 | Microbial Chem Res Found | New process for producing 3:4'-dideoxi-kanamycin b |
| CA2654561A1 (en) * | 2006-06-02 | 2007-12-13 | Meiji Seika Kaisha, Ltd. | Novel aminoglycoside antibiotics |
-
1971
- 1971-06-01 GB GB1831771A patent/GB1349302A/en not_active Expired
- 1971-06-02 IL IL36973A patent/IL36973A/xx unknown
- 1971-06-18 FI FI1744/71A patent/FI57596C/fi active
- 1971-06-23 ES ES392570A patent/ES392570A1/es not_active Expired
- 1971-06-25 CH CH937771A patent/CH552586A/xx not_active IP Right Cessation
- 1971-06-29 NL NL7109001.A patent/NL163219C/xx not_active IP Right Cessation
- 1971-07-19 HU HUZA335A patent/HU162704B/hu unknown
- 1971-07-23 SU SU1685994A patent/SU511007A3/ru active
- 1971-07-26 RO RO7100067797A patent/RO63815A/ro unknown
- 1971-07-27 YU YU1963/71A patent/YU35895B/xx unknown
- 1971-07-28 DK DK371271AA patent/DK127778B/da unknown
- 1971-07-28 CA CA119,288A patent/CA953294A/en not_active Expired
- 1971-07-28 LU LU63625D patent/LU63625A1/xx unknown
- 1971-07-28 AT AT657571A patent/AT320846B/de not_active IP Right Cessation
- 1971-07-28 FR FR7128504A patent/FR2103935A5/fr not_active Expired
- 1971-07-28 PL PL1971149704A patent/PL83206B1/pl unknown
- 1971-07-28 NO NO2852/71A patent/NO134117C/no unknown
- 1971-07-28 IE IE964/71A patent/IE35480B1/xx unknown
- 1971-07-29 BE BE770692A patent/BE770692A/xx unknown
- 1971-07-29 SE SE7109756A patent/SE398753B/xx unknown
- 1971-07-29 BG BG018187A patent/BG19188A3/xx unknown
-
1977
- 1977-11-17 HK HK574/77A patent/HK57477A/xx unknown
-
1978
- 1978-12-30 MY MY147/78A patent/MY7800147A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134117B (en, 2012) | 1976-05-10 |
| MY7800147A (en) | 1978-12-31 |
| CH552586A (de) | 1974-08-15 |
| FI57596B (fi) | 1980-05-30 |
| NO134117C (en, 2012) | 1976-08-18 |
| FR2103935A5 (en, 2012) | 1972-04-14 |
| NL7109001A (en, 2012) | 1972-02-01 |
| IL36973A (en) | 1974-06-30 |
| GB1349302A (en) | 1974-04-03 |
| SE398753B (sv) | 1978-01-16 |
| YU196371A (en) | 1981-02-28 |
| CA953294A (en) | 1974-08-20 |
| ES392570A1 (es) | 1974-06-16 |
| DE2135191B2 (de) | 1976-09-02 |
| RO63815A (fr) | 1979-01-15 |
| BE770692A (fr) | 1971-12-01 |
| NL163219C (nl) | 1980-08-15 |
| IE35480B1 (en) | 1976-03-03 |
| NL163219B (nl) | 1980-03-17 |
| HU162704B (en, 2012) | 1973-03-28 |
| DK127778B (da) | 1974-01-07 |
| YU35895B (en) | 1981-08-31 |
| DE2135191A1 (en, 2012) | 1972-02-03 |
| AT320846B (de) | 1975-02-25 |
| BG19188A3 (bg) | 1975-04-30 |
| HK57477A (en) | 1977-11-25 |
| LU63625A1 (en, 2012) | 1971-11-26 |
| PL83206B1 (en) | 1975-12-31 |
| IE35480L (en) | 1972-01-29 |
| SU511007A3 (ru) | 1976-04-15 |
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