PL81441B1 - - Google Patents
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- Publication number
- PL81441B1 PL81441B1 PL1971151754A PL15175471A PL81441B1 PL 81441 B1 PL81441 B1 PL 81441B1 PL 1971151754 A PL1971151754 A PL 1971151754A PL 15175471 A PL15175471 A PL 15175471A PL 81441 B1 PL81441 B1 PL 81441B1
- Authority
- PL
- Poland
- Prior art keywords
- thebaine
- base
- acid
- acid hydrazide
- dihydrothebaine
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 46
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 claims description 31
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 claims description 31
- 229930003945 thebaine Natural products 0.000 claims description 31
- XJZOLKDBHJPTAT-ATNYCFDYSA-N (4r,4ar,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical compound C([C@@H](N(CC1)C)[C@@H]2CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 XJZOLKDBHJPTAT-ATNYCFDYSA-N 0.000 claims description 20
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 15
- 229910000071 diazene Inorganic materials 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003974 aralkylamines Chemical class 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 125000000623 heterocyclic group Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 31
- 239000002585 base Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 238000009835 boiling Methods 0.000 description 9
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 9
- 229960000240 hydrocodone Drugs 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 hydrazine imine Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VKHZYWVEBNIRLX-UHFFFAOYSA-N methanesulfonohydrazide Chemical compound CS(=O)(=O)NN VKHZYWVEBNIRLX-UHFFFAOYSA-N 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RVJQWONQPCTLDL-SSTWWWIQSA-N (4r,4ar,7s,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical compound C([C@@H](N(CC1)C)[C@@H]2CC[C@@H]3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 RVJQWONQPCTLDL-SSTWWWIQSA-N 0.000 description 1
- ZGZUIGVCZUSCRV-UHFFFAOYSA-N 2-(1-cyclopropylethyl)-4-methylpyrazol-3-amine Chemical compound N1=CC(C)=C(N)N1C(C)C1CC1 ZGZUIGVCZUSCRV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000004156 Azodicarbonamide Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- XYYVYLMBEZUESM-CMKMFDCUSA-N codeinone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=CC(=O)[C@@H]1OC1=C2C3=CC=C1OC XYYVYLMBEZUESM-CMKMFDCUSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XBCFRZRVCDUSGX-UHFFFAOYSA-N phenylmethanesulfonohydrazide Chemical compound NNS(=O)(=O)CC1=CC=CC=C1 XBCFRZRVCDUSGX-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5892670 | 1970-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81441B1 true PL81441B1 (forum.php) | 1975-08-30 |
Family
ID=10482707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971151754A PL81441B1 (forum.php) | 1970-12-11 | 1971-11-24 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3812132A (forum.php) |
| JP (1) | JPS5511678B1 (forum.php) |
| AU (1) | AU459401B2 (forum.php) |
| BE (1) | BE776304A (forum.php) |
| CA (1) | CA958412A (forum.php) |
| CH (1) | CH556340A (forum.php) |
| CS (1) | CS176251B2 (forum.php) |
| DE (1) | DE2159348A1 (forum.php) |
| DK (1) | DK139974B (forum.php) |
| FR (1) | FR2117924B1 (forum.php) |
| GB (1) | GB1317210A (forum.php) |
| HU (1) | HU164465B (forum.php) |
| IL (1) | IL38268A (forum.php) |
| NL (1) | NL175622C (forum.php) |
| PL (1) | PL81441B1 (forum.php) |
| SE (1) | SE388422B (forum.php) |
| YU (1) | YU39064B (forum.php) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59142770A (ja) * | 1983-02-02 | 1984-08-16 | Trio Kenwood Corp | カセツトテ−プレコ−ダの駆動機構 |
| GB2429206A (en) * | 2004-07-09 | 2007-02-21 | Tasmanian Alkaloids Pty Ltd | Process for the synthesis of hydromorphone |
| US20080125592A1 (en) * | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| CA2674915C (en) | 2006-10-17 | 2015-06-30 | Penick Corporation | Process for preparing oxymorphone |
| WO2008048711A1 (en) | 2006-10-17 | 2008-04-24 | Penick Corporation | Process for preparing oxymorphone |
| GB0624880D0 (en) * | 2006-12-14 | 2007-01-24 | Johnson Matthey Plc | Improved method for making analgesics |
| US9131649B2 (en) * | 2008-03-07 | 2015-09-15 | Tasmanian Alkaloids Pty. Ltd | Papaver somniferum strain with high concentration of thebaine |
| US8541647B2 (en) | 2008-05-29 | 2013-09-24 | Tasmania Alkaloids Pty, Ltd. | Papaver somniferum with high concentration of codeine |
| AU2010298514B2 (en) * | 2009-09-22 | 2014-11-20 | SpecGx LLC | Methods for producing hydrocodone, hydromorphone or a derivative thereof |
| CA2802294C (en) | 2010-06-11 | 2016-05-10 | Rhodes Technologies | Process for n-dealkylation of tertiary amines |
| JP5736040B2 (ja) | 2010-06-11 | 2015-06-17 | ローズ テクノロジーズ | Ｎ−アリル化合物の調製のための遷移金属触媒プロセスおよびその使用 |
| US9120800B2 (en) | 2013-08-02 | 2015-09-01 | Johnson Matthey Public Limited Company | Process for the preparation of oxymorphone alkaloid and oxymorphone salts |
| US9273060B2 (en) | 2014-03-05 | 2016-03-01 | Johnson Matthey Public Limited Company | Processes for making hydrocodone, hydromorphone and their derivatives |
| WO2015134003A1 (en) | 2014-03-05 | 2015-09-11 | Johnson Matthey Public Limited Company | Processes for making hydrocodone, hydromorphone and their derivatives |
| US10155771B2 (en) | 2015-11-04 | 2018-12-18 | Noramco, Inc. | Selective reduction of morphinan alkaloids |
-
1970
- 1970-12-11 GB GB5892670A patent/GB1317210A/en not_active Expired
-
1971
- 1971-11-24 PL PL1971151754A patent/PL81441B1/pl unknown
- 1971-11-30 IL IL38268A patent/IL38268A/en unknown
- 1971-11-30 CA CA128,915A patent/CA958412A/en not_active Expired
- 1971-11-30 DE DE19712159348 patent/DE2159348A1/de not_active Withdrawn
- 1971-12-02 US US00204298A patent/US3812132A/en not_active Expired - Lifetime
- 1971-12-03 AU AU36469/71A patent/AU459401B2/en not_active Expired
- 1971-12-06 BE BE776304A patent/BE776304A/xx not_active IP Right Cessation
- 1971-12-07 FR FR7143867A patent/FR2117924B1/fr not_active Expired
- 1971-12-07 JP JP9899371A patent/JPS5511678B1/ja active Pending
- 1971-12-09 YU YU03086/71A patent/YU39064B/xx unknown
- 1971-12-09 DK DK603371AA patent/DK139974B/da unknown
- 1971-12-09 CS CS8571A patent/CS176251B2/cs unknown
- 1971-12-10 SE SE7115886A patent/SE388422B/xx unknown
- 1971-12-10 CH CH1811571A patent/CH556340A/xx not_active IP Right Cessation
- 1971-12-10 HU HUMA2294A patent/HU164465B/hu unknown
- 1971-12-13 NL NLAANVRAGE7117082,A patent/NL175622C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE776304A (fr) | 1972-06-06 |
| CS176251B2 (forum.php) | 1977-06-30 |
| IL38268A0 (en) | 1972-01-27 |
| GB1317210A (en) | 1973-05-16 |
| HU164465B (forum.php) | 1974-02-28 |
| YU308671A (en) | 1982-06-30 |
| IL38268A (en) | 1974-11-29 |
| DK139974B (da) | 1979-05-28 |
| FR2117924B1 (forum.php) | 1975-02-07 |
| DE2159348A1 (de) | 1972-06-15 |
| US3812132A (en) | 1974-05-21 |
| NL175622C (nl) | 1984-12-03 |
| FR2117924A1 (forum.php) | 1972-07-28 |
| CA958412A (en) | 1974-11-26 |
| YU39064B (en) | 1984-04-30 |
| NL175622B (nl) | 1984-07-02 |
| AU3646971A (en) | 1973-06-07 |
| CH556340A (de) | 1974-11-29 |
| AU459401B2 (en) | 1975-03-27 |
| SE388422B (sv) | 1976-10-04 |
| NL7117082A (forum.php) | 1972-06-13 |
| DK139974C (forum.php) | 1979-12-10 |
| JPS5511678B1 (forum.php) | 1980-03-26 |
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