PL90720B1 - - Google Patents
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- Publication number
- PL90720B1 PL90720B1 PL1973174968A PL17496873A PL90720B1 PL 90720 B1 PL90720 B1 PL 90720B1 PL 1973174968 A PL1973174968 A PL 1973174968A PL 17496873 A PL17496873 A PL 17496873A PL 90720 B1 PL90720 B1 PL 90720B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- chloroform
- compounds
- water
- solution
- Prior art date
Links
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- -1 lithium aluminum hydride Chemical compound 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- NGPGDYLVALNKEG-OLXYHTOASA-N diammonium L-tartrate Chemical compound [NH4+].[NH4+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O NGPGDYLVALNKEG-OLXYHTOASA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 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
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 239000012071 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
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 208000004224 Opium Dependence Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- HKOIXWVRNLGFOR-KOFBORESSA-N norcodeine Chemical compound O[C@H]([C@@H]1O2)C=C[C@H]3[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4 HKOIXWVRNLGFOR-KOFBORESSA-N 0.000 description 1
- 229950004392 norcodeine Drugs 0.000 description 1
- HKOIXWVRNLGFOR-UHFFFAOYSA-N norcodeine Natural products O1C2C(O)C=CC3C4CC5=CC=C(OC)C1=C5C23CCN4 HKOIXWVRNLGFOR-UHFFFAOYSA-N 0.000 description 1
- 229950006134 normorphine Drugs 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 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 |
|---|---|
| PL90720B1 true PL90720B1 (en, 2012) | 1977-01-31 |
Family
ID=5856355
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973174974A PL91809B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174969A PL91837B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174970A PL91836B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174971A PL91829B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174972A PL91807B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973165187A PL87721B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174973A PL91808B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174968A PL90720B1 (en, 2012) | 1972-09-14 | 1973-09-13 |
Family Applications Before (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973174974A PL91809B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174969A PL91837B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174970A PL91836B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174971A PL91829B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174972A PL91807B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973165187A PL87721B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174973A PL91808B1 (en, 2012) | 1972-09-14 | 1973-09-13 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3928359A (en, 2012) |
| JP (1) | JPS4966700A (en, 2012) |
| AT (1) | AT326281B (en, 2012) |
| BE (1) | BE804836A (en, 2012) |
| BG (8) | BG21229A3 (en, 2012) |
| CH (7) | CH589089A5 (en, 2012) |
| CS (8) | CS168673B2 (en, 2012) |
| DD (1) | DD109384A5 (en, 2012) |
| DE (1) | DE2245141A1 (en, 2012) |
| ES (8) | ES418563A1 (en, 2012) |
| FI (1) | FI55512C (en, 2012) |
| FR (1) | FR2199982B1 (en, 2012) |
| GB (1) | GB1449222A (en, 2012) |
| HU (1) | HU166367B (en, 2012) |
| IE (1) | IE38320B1 (en, 2012) |
| IL (1) | IL43216A (en, 2012) |
| NL (1) | NL7312621A (en, 2012) |
| NO (1) | NO139482C (en, 2012) |
| PL (8) | PL91809B1 (en, 2012) |
| RO (2) | RO70193A (en, 2012) |
| SE (1) | SE413510B (en, 2012) |
| SU (8) | SU498911A3 (en, 2012) |
| YU (2) | YU243973A (en, 2012) |
| ZA (1) | ZA737289B (en, 2012) |
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
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