SU535903A3 - Способ получени замещенных бигуанидов - Google Patents
Способ получени замещенных бигуанидовInfo
- Publication number
- SU535903A3 SU535903A3 SU1767915A SU1767915A SU535903A3 SU 535903 A3 SU535903 A3 SU 535903A3 SU 1767915 A SU1767915 A SU 1767915A SU 1767915 A SU1767915 A SU 1767915A SU 535903 A3 SU535903 A3 SU 535903A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- unsaturated
- saturated
- straight
- branched hydrocarbon
- Prior art date
Links
- 229940123208 Biguanide Drugs 0.000 title claims description 6
- 150000004283 biguanides Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910000464 lead oxide Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910000474 mercury oxide Inorganic materials 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960004198 guanidine Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- -1 hydrochloric Chemical class 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- BWBKOTRFVFLABK-UHFFFAOYSA-N 1,2-dibutyl-3-(diaminomethylidene)guanidine;hydrochloride Chemical compound Cl.CCCCNC(NC(N)=N)=NCCCC BWBKOTRFVFLABK-UHFFFAOYSA-N 0.000 description 1
- KREOCUNMMFZOOS-UHFFFAOYSA-N 1,3-di(propan-2-yl)thiourea Chemical compound CC(C)NC(S)=NC(C)C KREOCUNMMFZOOS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C1/00—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design
- A61C1/02—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools
- A61C1/05—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive
- A61C1/057—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive with means for preventing suction effect in turbine after deactivation of the drive air
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dentistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117015 DE2117015A1 (de) | 1971-04-02 | 1971-04-02 | 1,2-Biguanide |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1907668A Division SU493959A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени 1,2-бигуанидов |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU535903A3 true SU535903A3 (ru) | 1976-11-15 |
Family
ID=5804148
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1767915A SU535903A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанидов |
| SU1907665A SU465784A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
| SU1907668A SU493959A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени 1,2-бигуанидов |
| SU1907667A SU472501A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1907665A SU465784A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
| SU1907668A SU493959A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени 1,2-бигуанидов |
| SU1907667A SU472501A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
Country Status (19)
| Country | Link |
|---|---|
| AR (3) | AR194360A1 (enExample) |
| AT (4) | AT317239B (enExample) |
| AU (1) | AU468307B2 (enExample) |
| BE (1) | BE781590A (enExample) |
| CA (1) | CA988084A (enExample) |
| CH (1) | CH579534A5 (enExample) |
| CS (3) | CS161935B2 (enExample) |
| DD (1) | DD95228A5 (enExample) |
| DE (1) | DE2117015A1 (enExample) |
| DK (1) | DK129651B (enExample) |
| ES (1) | ES401124A1 (enExample) |
| FR (1) | FR2132396B1 (enExample) |
| GB (1) | GB1386130A (enExample) |
| HU (1) | HU162902B (enExample) |
| NL (1) | NL7204493A (enExample) |
| NO (1) | NO135418C (enExample) |
| SE (1) | SE377332B (enExample) |
| SU (4) | SU535903A3 (enExample) |
| ZA (1) | ZA722183B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008007314A1 (de) | 2008-02-02 | 2009-08-06 | Merck Patent Gmbh | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5-triazinderivaten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR940304A (fr) * | 1946-01-07 | 1948-12-09 | Ici Ltd | Procédé de fabrication de dérivés de biguanides |
-
1971
- 1971-04-02 DE DE19712117015 patent/DE2117015A1/de not_active Withdrawn
-
1972
- 1972-03-15 CS CS1724A patent/CS161935B2/cs unknown
- 1972-03-15 CS CS6963*A patent/CS161936B2/cs unknown
- 1972-03-15 CS CS6964*A patent/CS161937B2/cs unknown
- 1972-03-22 DK DK134572AA patent/DK129651B/da unknown
- 1972-03-23 ES ES401124A patent/ES401124A1/es not_active Expired
- 1972-03-27 GB GB1416272A patent/GB1386130A/en not_active Expired
- 1972-03-27 CH CH454672A patent/CH579534A5/xx not_active IP Right Cessation
- 1972-03-29 AR AR241248A patent/AR194360A1/es active
- 1972-03-29 NO NO1084/72A patent/NO135418C/no unknown
- 1972-03-29 SE SE7204127A patent/SE377332B/xx unknown
- 1972-03-30 AT AT00784/73A patent/AT317239B/de not_active IP Right Cessation
- 1972-03-30 AT AT279272A patent/AT313301B/de not_active IP Right Cessation
- 1972-03-30 HU HUSC383A patent/HU162902B/hu unknown
- 1972-03-30 DD DD161938A patent/DD95228A5/xx unknown
- 1972-03-30 ZA ZA722183A patent/ZA722183B/xx unknown
- 1972-03-30 AT AT00786/73A patent/AT321318B/de not_active IP Right Cessation
- 1972-03-30 AT AT00785/73A patent/AT317240B/de not_active IP Right Cessation
- 1972-03-30 AU AU40661/72A patent/AU468307B2/en not_active Expired
- 1972-03-31 SU SU1767915A patent/SU535903A3/ru active
- 1972-03-31 SU SU1907665A patent/SU465784A3/ru active
- 1972-03-31 BE BE781590A patent/BE781590A/xx unknown
- 1972-03-31 SU SU1907668A patent/SU493959A3/ru active
- 1972-03-31 SU SU1907667A patent/SU472501A3/ru active
- 1972-04-04 NL NL7204493A patent/NL7204493A/xx not_active Application Discontinuation
- 1972-04-04 FR FR7211727A patent/FR2132396B1/fr not_active Expired
- 1972-04-04 CA CA138,838A patent/CA988084A/en not_active Expired
- 1972-11-13 AR AR245079A patent/AR194285A1/es active
- 1972-11-13 AR AR245080A patent/AR192485A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AT317240B (de) | 1974-08-26 |
| DK129651B (da) | 1974-11-04 |
| CS161935B2 (enExample) | 1975-06-10 |
| NO135418B (enExample) | 1976-12-27 |
| AT317239B (de) | 1974-08-26 |
| HU162902B (enExample) | 1973-04-28 |
| SU465784A3 (ru) | 1975-03-30 |
| ES401124A1 (es) | 1975-02-16 |
| BE781590A (fr) | 1972-10-02 |
| AU4066172A (en) | 1973-10-04 |
| SU472501A3 (ru) | 1975-05-30 |
| CS161936B2 (enExample) | 1975-06-10 |
| NO135418C (enExample) | 1977-04-05 |
| CA988084A (en) | 1976-04-27 |
| AR192485A1 (es) | 1973-02-21 |
| DE2117015A1 (de) | 1972-10-26 |
| DK129651C (enExample) | 1975-04-07 |
| CS161937B2 (enExample) | 1975-06-10 |
| DD95228A5 (enExample) | 1973-01-20 |
| SE377332B (enExample) | 1975-06-30 |
| AU468307B2 (en) | 1973-10-04 |
| AR194285A1 (es) | 1973-06-29 |
| NL7204493A (enExample) | 1972-10-04 |
| AR194360A1 (es) | 1973-07-13 |
| FR2132396A1 (enExample) | 1972-11-17 |
| FR2132396B1 (enExample) | 1975-10-10 |
| GB1386130A (en) | 1975-03-05 |
| SU493959A3 (ru) | 1975-11-28 |
| AT321318B (de) | 1975-03-25 |
| CH579534A5 (enExample) | 1976-09-15 |
| ZA722183B (en) | 1972-12-27 |
| AT313301B (de) | 1974-02-11 |
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