NO135525B - - Google Patents
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- Publication number
- NO135525B NO135525B NO721267A NO126772A NO135525B NO 135525 B NO135525 B NO 135525B NO 721267 A NO721267 A NO 721267A NO 126772 A NO126772 A NO 126772A NO 135525 B NO135525 B NO 135525B
- Authority
- NO
- Norway
- Prior art keywords
- pyridone
- dimethyl
- dicarboethoxy
- dose
- reacted
- Prior art date
Links
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 23
- 241000700159 Rattus Species 0.000 description 20
- 206010030113 Oedema Diseases 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 235000010418 carrageenan Nutrition 0.000 description 15
- 229920001525 carrageenan Polymers 0.000 description 15
- 230000002401 inhibitory effect Effects 0.000 description 11
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001562 ulcerogenic effect Effects 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- -1 2,6-dimethyl-3,5-dicarboethoxy-N-(4'-isobutoxyphenyl)-4-pyridone Chemical compound 0.000 description 1
- JIJYSZFTNISEKP-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-1-phenylpyridine-3,5-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C(C(O)=O)=C(C)N1C1=CC=CC=C1 JIJYSZFTNISEKP-UHFFFAOYSA-N 0.000 description 1
- NDHJFACYRWUMHT-UHFFFAOYSA-N 4-(2-methylpropoxy)aniline Chemical compound CC(C)COC1=CC=C(N)C=C1 NDHJFACYRWUMHT-UHFFFAOYSA-N 0.000 description 1
- DJRKHTCUXRGYEU-UHFFFAOYSA-N 4-Hexyloxyaniline Chemical compound CCCCCCOC1=CC=C(N)C=C1 DJRKHTCUXRGYEU-UHFFFAOYSA-N 0.000 description 1
- UBRIHZOFEJHMIT-UHFFFAOYSA-N 4-butoxyaniline Chemical compound CCCCOC1=CC=C(N)C=C1 UBRIHZOFEJHMIT-UHFFFAOYSA-N 0.000 description 1
- SNTDJOBXSWWDSN-UHFFFAOYSA-N 4-cyclohexyloxyaniline Chemical compound C1=CC(N)=CC=C1OC1CCCCC1 SNTDJOBXSWWDSN-UHFFFAOYSA-N 0.000 description 1
- XWGJQNKDSHYJID-UHFFFAOYSA-N 4-decoxyaniline Chemical compound CCCCCCCCCCOC1=CC=C(N)C=C1 XWGJQNKDSHYJID-UHFFFAOYSA-N 0.000 description 1
- SDMJIFBABYOTNO-UHFFFAOYSA-N 4-heptadecoxyaniline Chemical compound CCCCCCCCCCCCCCCCCOC1=CC=C(N)C=C1 SDMJIFBABYOTNO-UHFFFAOYSA-N 0.000 description 1
- LTGYTOOKQWFTQG-UHFFFAOYSA-N 4-heptoxyaniline Chemical compound CCCCCCCOC1=CC=C(N)C=C1 LTGYTOOKQWFTQG-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- VHLNNLJPJGVFRU-UHFFFAOYSA-N 4-octadecoxyaniline Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=C(N)C=C1 VHLNNLJPJGVFRU-UHFFFAOYSA-N 0.000 description 1
- ACYGZCHBIGKPGR-UHFFFAOYSA-N 4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N)C=C1 ACYGZCHBIGKPGR-UHFFFAOYSA-N 0.000 description 1
- ZMPUYJLKSUAQEJ-UHFFFAOYSA-N 4-pentadecoxyaniline Chemical compound C(CCCCCCCCCCCCCC)OC1=CC=C(N)C=C1 ZMPUYJLKSUAQEJ-UHFFFAOYSA-N 0.000 description 1
- DGFTWBUZRHAHTH-UHFFFAOYSA-N 4-pentylaniline Chemical compound CCCCCC1=CC=C(N)C=C1 DGFTWBUZRHAHTH-UHFFFAOYSA-N 0.000 description 1
- SGHYUZKXTRJREF-UHFFFAOYSA-N 4-tetradecoxyaniline Chemical compound CCCCCCCCCCCCCCOC1=CC=C(N)C=C1 SGHYUZKXTRJREF-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LXWFHMREWLOKLM-UHFFFAOYSA-N CP-24879 Chemical compound CC(C)CCOC1=CC=C(N)C=C1 LXWFHMREWLOKLM-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- RMNODPKXKCEZGA-UHFFFAOYSA-N diethyl 1-(3-hydroxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C)N1C1=CC=CC(O)=C1 RMNODPKXKCEZGA-UHFFFAOYSA-N 0.000 description 1
- BVNXAQNPJKGNDY-UHFFFAOYSA-N diethyl 1-(4-decoxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1N1C(C)=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C1C BVNXAQNPJKGNDY-UHFFFAOYSA-N 0.000 description 1
- UIDJVDPZJDSHBF-UHFFFAOYSA-N diethyl 1-(4-ethoxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C)N1C1=CC=C(OCC)C=C1 UIDJVDPZJDSHBF-UHFFFAOYSA-N 0.000 description 1
- PTTLJTDLHKHXQS-UHFFFAOYSA-N diethyl 1-(4-heptoxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound C1=CC(OCCCCCCC)=CC=C1N1C(C)=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C1C PTTLJTDLHKHXQS-UHFFFAOYSA-N 0.000 description 1
- FXFVJFVNSKYXMX-UHFFFAOYSA-N diethyl 1-(4-hydroxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C)N1C1=CC=C(O)C=C1 FXFVJFVNSKYXMX-UHFFFAOYSA-N 0.000 description 1
- LBXPBWOPBMIWQX-UHFFFAOYSA-N diethyl 1-(4-methoxyphenyl)-2,6-dimethyl-4-oxopyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C)N1C1=CC=C(OC)C=C1 LBXPBWOPBMIWQX-UHFFFAOYSA-N 0.000 description 1
- NAJWTVWGFUSZBQ-UHFFFAOYSA-N diethyl 2,6-dimethyl-1-(4-octadecoxyphenyl)-4-oxopyridine-3,5-dicarboxylate Chemical compound C1=CC(OCCCCCCCCCCCCCCCCCC)=CC=C1N1C(C)=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C1C NAJWTVWGFUSZBQ-UHFFFAOYSA-N 0.000 description 1
- YMLQBGPTRPRRSH-UHFFFAOYSA-N diethyl 2,6-dimethyl-1-[4-(3-methylbutoxy)phenyl]-4-oxopyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C)N1C1=CC=C(OCCC(C)C)C=C1 YMLQBGPTRPRRSH-UHFFFAOYSA-N 0.000 description 1
- HRHNYVANBRTEQO-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-oxo-1-(4-propoxyphenyl)pyridine-3,5-dicarboxylate Chemical compound C1=CC(OCCC)=CC=C1N1C(C)=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C1C HRHNYVANBRTEQO-UHFFFAOYSA-N 0.000 description 1
- JISSLTOKQRHSMJ-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-oxopyran-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)OC(C)=C(C(=O)OCC)C1=O JISSLTOKQRHSMJ-UHFFFAOYSA-N 0.000 description 1
- PVBALTLWZVEAIO-UHFFFAOYSA-N diodone Chemical compound OC(=O)CN1C=C(I)C(=O)C(I)=C1 PVBALTLWZVEAIO-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000033687 granuloma formation Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL36627A IL36627A (en) | 1971-04-14 | 1971-04-14 | 2,6-dimethyl-3,5-dialkoxy(aralkoxy)carbonyl-4-pyridone derivatives,their preparation and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135525B true NO135525B (ru) | 1977-01-10 |
| NO135525C NO135525C (ru) | 1977-04-20 |
Family
ID=11045876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO721267A NO135525C (ru) | 1971-04-14 | 1972-04-13 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4839482A (ru) |
| AT (1) | AT320647B (ru) |
| AU (1) | AU468109B2 (ru) |
| BE (1) | BE781925A (ru) |
| CA (1) | CA1002954A (ru) |
| CH (1) | CH587824A5 (ru) |
| DE (1) | DE2217739A1 (ru) |
| DK (1) | DK129522B (ru) |
| ES (1) | ES402696A1 (ru) |
| FI (1) | FI55189C (ru) |
| FR (1) | FR2133655B1 (ru) |
| GB (1) | GB1379786A (ru) |
| IE (1) | IE36293B1 (ru) |
| IL (1) | IL36627A (ru) |
| NL (1) | NL7205007A (ru) |
| NO (1) | NO135525C (ru) |
| SE (1) | SE376611B (ru) |
| ZA (1) | ZA722432B (ru) |
-
1971
- 1971-04-14 IL IL36627A patent/IL36627A/xx unknown
-
1972
- 1972-04-05 GB GB1558272A patent/GB1379786A/en not_active Expired
- 1972-04-07 CH CH518072A patent/CH587824A5/xx not_active IP Right Cessation
- 1972-04-10 AU AU40934/72A patent/AU468109B2/en not_active Expired
- 1972-04-11 ZA ZA722432A patent/ZA722432B/xx unknown
- 1972-04-11 BE BE781925A patent/BE781925A/xx unknown
- 1972-04-12 CA CA139,531A patent/CA1002954A/en not_active Expired
- 1972-04-12 FI FI1023/72A patent/FI55189C/fi active
- 1972-04-13 AT AT320172A patent/AT320647B/de not_active IP Right Cessation
- 1972-04-13 JP JP47036549A patent/JPS4839482A/ja active Pending
- 1972-04-13 FR FR7212887A patent/FR2133655B1/fr not_active Expired
- 1972-04-13 NO NO721267A patent/NO135525C/no unknown
- 1972-04-13 DE DE19722217739 patent/DE2217739A1/de active Pending
- 1972-04-13 SE SE7204795A patent/SE376611B/xx unknown
- 1972-04-13 DK DK180372AA patent/DK129522B/da unknown
- 1972-04-14 IE IE497/72A patent/IE36293B1/xx unknown
- 1972-04-14 NL NL7205007A patent/NL7205007A/xx not_active Application Discontinuation
- 1972-04-14 ES ES402696A patent/ES402696A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO135525C (ru) | 1977-04-20 |
| IE36293B1 (en) | 1976-09-29 |
| AU468109B2 (en) | 1973-10-18 |
| DK129522C (ru) | 1975-04-14 |
| DK129522B (da) | 1974-10-21 |
| IE36293L (en) | 1972-10-14 |
| FI55189B (fi) | 1979-02-28 |
| IL36627A0 (en) | 1971-06-23 |
| FR2133655B1 (ru) | 1975-10-10 |
| IL36627A (en) | 1975-03-13 |
| GB1379786A (en) | 1975-01-08 |
| AT320647B (de) | 1975-02-25 |
| FI55189C (fi) | 1979-06-11 |
| FR2133655A1 (ru) | 1972-12-01 |
| AU4093472A (en) | 1973-10-18 |
| ES402696A1 (es) | 1975-04-01 |
| JPS4839482A (ru) | 1973-06-09 |
| CA1002954A (en) | 1977-01-04 |
| SE376611B (ru) | 1975-06-02 |
| DE2217739A1 (de) | 1972-10-26 |
| ZA722432B (en) | 1973-08-29 |
| BE781925A (fr) | 1972-10-11 |
| NL7205007A (ru) | 1972-10-17 |
| CH587824A5 (ru) | 1977-05-13 |
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