SU498911A3 - Способ получени производных -(гетероарилметил) - -дезоксинорморфинов или -дезоксиноркодеинов - Google Patents
Способ получени производных -(гетероарилметил) - -дезоксинорморфинов или -дезоксиноркодеиновInfo
- Publication number
- SU498911A3 SU498911A3 SU1962620A SU1962620A SU498911A3 SU 498911 A3 SU498911 A3 SU 498911A3 SU 1962620 A SU1962620 A SU 1962620A SU 1962620 A SU1962620 A SU 1962620A SU 498911 A3 SU498911 A3 SU 498911A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- deoxynormorphins
- deoxyninorcodeins
- heteroarylmethyl
- obtaining derivatives
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 229960004126 codeine Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-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
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- -1 triethylamine Chemical class 0.000 description 2
- WECUIJXZKLGURU-UHFFFAOYSA-N 3-(chloromethyl)furan Chemical compound ClCC=1C=COC=1 WECUIJXZKLGURU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920006051 Capron® Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ONBWJWYUHXVEJS-ZTYRTETDSA-N Normorphine Chemical class C([C@@H](NCC1)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ONBWJWYUHXVEJS-ZTYRTETDSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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:
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Networks Using Active Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2245141A DE2245141A1 (de) | 1972-09-14 | 1972-09-14 | Neue n-(heteroarylmethyl)-desoxynormorphine und -norcodeine, deren saeureadditionssalze, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU498911A3 true SU498911A3 (ru) | 1976-01-05 |
Family
ID=5856355
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1962620A SU498911A3 (ru) | 1972-09-14 | 1973-09-12 | Способ получени производных -(гетероарилметил) - -дезоксинорморфинов или -дезоксиноркодеинов |
| SU2063986A SU505366A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -/гетероарилметилдезокси-норморфинов или-норкодеинов |
| SU2063380A SU503524A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил) -дезокси-норморфинов или -норкодеинов |
| SU2063983A SU509239A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарил-метил)- 7-дезокси-норморфиновили -норкодеинов |
| SU2063987A SU506299A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил)дезоксинорморфинов или -норкодеинов |
| SU2063985A SU503523A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил)- -дезокси-нормофинов или -норкодеинов |
| SU2063984A SU520049A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени (гетероарилметил)- дезокси-норморфинов или их дигидросоединений или их солей |
| SU2063982A SU528878A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени производных (гетероарилметил)-дезоксинорморфина или- дезоксиноркодеина, или их солей |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2063986A SU505366A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -/гетероарилметилдезокси-норморфинов или-норкодеинов |
| SU2063380A SU503524A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил) -дезокси-норморфинов или -норкодеинов |
| SU2063983A SU509239A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарил-метил)- 7-дезокси-норморфиновили -норкодеинов |
| SU2063987A SU506299A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил)дезоксинорморфинов или -норкодеинов |
| SU2063985A SU503523A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени -(гетероарилметил)- -дезокси-нормофинов или -норкодеинов |
| SU2063984A SU520049A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени (гетероарилметил)- дезокси-норморфинов или их дигидросоединений или их солей |
| SU2063982A SU528878A3 (ru) | 1972-09-14 | 1974-09-30 | Способ получени производных (гетероарилметил)-дезоксинорморфина или- дезоксиноркодеина, или их солей |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3928359A (OSRAM) |
| JP (1) | JPS4966700A (OSRAM) |
| AT (1) | AT326281B (OSRAM) |
| BE (1) | BE804836A (OSRAM) |
| BG (8) | BG21229A3 (OSRAM) |
| CH (7) | CH589089A5 (OSRAM) |
| CS (8) | CS168673B2 (OSRAM) |
| DD (1) | DD109384A5 (OSRAM) |
| DE (1) | DE2245141A1 (OSRAM) |
| ES (8) | ES418563A1 (OSRAM) |
| FI (1) | FI55512C (OSRAM) |
| FR (1) | FR2199982B1 (OSRAM) |
| GB (1) | GB1449222A (OSRAM) |
| HU (1) | HU166367B (OSRAM) |
| IE (1) | IE38320B1 (OSRAM) |
| IL (1) | IL43216A (OSRAM) |
| NL (1) | NL7312621A (OSRAM) |
| NO (1) | NO139482C (OSRAM) |
| PL (8) | PL91809B1 (OSRAM) |
| RO (2) | RO70193A (OSRAM) |
| SE (1) | SE413510B (OSRAM) |
| SU (8) | SU498911A3 (OSRAM) |
| YU (2) | YU243973A (OSRAM) |
| ZA (1) | ZA737289B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4236008A (en) * | 1978-09-19 | 1980-11-25 | E. I. Du Pont De Nemours And Company | Fluorination of precursors for fluorine analogs of hydrocodone and oxycodone |
| US4241065A (en) * | 1979-07-02 | 1980-12-23 | E. I. Du Pont De Nemours And Company | Fluoro analogs of hydrocodone and oxycodone useful as analgesics, narcotic antagonists or both |
| CA2319627A1 (en) * | 1998-01-29 | 1999-08-05 | Polychip Pharmaceuticals Pty. Ltd. | Therapeutic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2107989A1 (de) * | 1971-02-19 | 1972-09-07 | Boehringer Sohn Ingelheim | N-(Furyl-methy])-morphinane, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
-
1972
- 1972-09-14 DE DE2245141A patent/DE2245141A1/de active Pending
-
1973
- 1973-09-03 AT AT761673A patent/AT326281B/de not_active IP Right Cessation
- 1973-09-07 ES ES418563A patent/ES418563A1/es not_active Expired
- 1973-09-11 CH CH198177A patent/CH589089A5/xx not_active IP Right Cessation
- 1973-09-11 US US396171A patent/US3928359A/en not_active Expired - Lifetime
- 1973-09-11 CH CH207077A patent/CH591490A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207377A patent/CH591491A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH198077A patent/CH589088A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207277A patent/CH605958A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207177A patent/CH589090A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH1298673A patent/CH590287A5/xx not_active IP Right Cessation
- 1973-09-12 BG BG025618A patent/BG21229A3/xx unknown
- 1973-09-12 BG BG025619A patent/BG21230A3/xx unknown
- 1973-09-12 CS CS6322A patent/CS168673B2/cs unknown
- 1973-09-12 DD DD173479A patent/DD109384A5/xx unknown
- 1973-09-12 CS CS283*[A patent/CS168675B2/cs unknown
- 1973-09-12 SU SU1962620A patent/SU498911A3/ru active
- 1973-09-12 CS CS282*[A patent/CS168674B2/cs unknown
- 1973-09-12 IE IE1630/73A patent/IE38320B1/xx unknown
- 1973-09-12 CS CS285*[A patent/CS168677B2/cs unknown
- 1973-09-12 CS CS284*[A patent/CS168676B2/cs unknown
- 1973-09-12 BG BG025616A patent/BG21227A3/xx unknown
- 1973-09-12 BG BG24524A patent/BG21412A3/xx unknown
- 1973-09-12 BG BG025614A patent/BG21225A3/xx unknown
- 1973-09-12 CS CS287*[A patent/CS168679B2/cs unknown
- 1973-09-12 CS CS288*[A patent/CS168680B2/cs unknown
- 1973-09-12 BG BG25617A patent/BG21228A3/xx unknown
- 1973-09-12 BG BG025613A patent/BG21224A3/xx unknown
- 1973-09-12 CS CS286*[A patent/CS168678B2/cs unknown
- 1973-09-12 HU HUBO1463A patent/HU166367B/hu unknown
- 1973-09-13 RO RO7382817A patent/RO70193A/ro unknown
- 1973-09-13 PL PL1973174974A patent/PL91809B1/pl unknown
- 1973-09-13 PL PL1973174969A patent/PL91837B1/pl unknown
- 1973-09-13 PL PL1973174970A patent/PL91836B1/pl unknown
- 1973-09-13 NO NO3588/73A patent/NO139482C/no unknown
- 1973-09-13 PL PL1973174971A patent/PL91829B1/pl unknown
- 1973-09-13 NL NL7312621A patent/NL7312621A/xx not_active Application Discontinuation
- 1973-09-13 JP JP48103716A patent/JPS4966700A/ja active Pending
- 1973-09-13 FI FI2853/73A patent/FI55512C/fi active
- 1973-09-13 IL IL43216A patent/IL43216A/en unknown
- 1973-09-13 PL PL1973174972A patent/PL91807B1/pl unknown
- 1973-09-13 BE BE135636A patent/BE804836A/xx unknown
- 1973-09-13 PL PL1973165187A patent/PL87721B1/pl unknown
- 1973-09-13 ZA ZA00737289A patent/ZA737289B/xx unknown
- 1973-09-13 PL PL1973174973A patent/PL91808B1/pl unknown
- 1973-09-13 YU YU02439/73A patent/YU243973A/xx unknown
- 1973-09-13 PL PL1973174968A patent/PL90720B1/pl unknown
- 1973-09-13 GB GB4314673A patent/GB1449222A/en not_active Expired
- 1973-09-13 RO RO7300076068A patent/RO63003A/ro unknown
- 1973-09-14 SE SE7312583A patent/SE413510B/xx unknown
- 1973-09-14 FR FR7333092A patent/FR2199982B1/fr not_active Expired
-
1974
- 1974-01-28 BG BG025615A patent/BG21226A3/bg unknown
- 1974-09-19 ES ES430199A patent/ES430199A1/es not_active Expired
- 1974-09-19 ES ES430201A patent/ES430201A1/es not_active Expired
- 1974-09-19 ES ES430200A patent/ES430200A1/es not_active Expired
- 1974-09-19 ES ES430203A patent/ES430203A1/es not_active Expired
- 1974-09-19 ES ES430202A patent/ES430202A1/es not_active Expired
- 1974-09-19 ES ES430198A patent/ES430198A1/es not_active Expired
- 1974-09-19 ES ES430197A patent/ES430197A1/es not_active Expired
- 1974-09-30 SU SU2063986A patent/SU505366A3/ru active
- 1974-09-30 SU SU2063380A patent/SU503524A3/ru active
- 1974-09-30 SU SU2063983A patent/SU509239A3/ru active
- 1974-09-30 SU SU2063987A patent/SU506299A3/ru active
- 1974-09-30 SU SU2063985A patent/SU503523A3/ru active
- 1974-09-30 SU SU2063984A patent/SU520049A3/ru active
- 1974-09-30 SU SU2063982A patent/SU528878A3/ru active
-
1979
- 1979-10-19 YU YU02548/79A patent/YU254879A/xx unknown
Also Published As
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