NO134986B - - Google Patents
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- Publication number
- NO134986B NO134986B NO1707/72A NO170772A NO134986B NO 134986 B NO134986 B NO 134986B NO 1707/72 A NO1707/72 A NO 1707/72A NO 170772 A NO170772 A NO 170772A NO 134986 B NO134986 B NO 134986B
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- pyridyl
- general formula
- acid
- residue
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000003182 bronchodilatating effect Effects 0.000 claims 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 claims 1
- -1 1-(6-aminonicotinamidoethyl)-4-(6-methyl-2-pyridyl)piperazine Chemical compound 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RXSLHYTZMIUANX-UHFFFAOYSA-N 6-acetamidopyridine-3-carboxylic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=N1 RXSLHYTZMIUANX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- DXFYXKZAUVHOJH-UHFFFAOYSA-N 1-(4-pyridin-2-ylpiperazin-1-yl)ethanamine Chemical compound NC(C)N1CCN(CC1)C1=NC=CC=C1 DXFYXKZAUVHOJH-UHFFFAOYSA-N 0.000 description 2
- 206010002199 Anaphylactic shock Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WPZGIHCOKAJSHJ-UHFFFAOYSA-N 5-acetamidopyridine-2-carboxylic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)N=C1 WPZGIHCOKAJSHJ-UHFFFAOYSA-N 0.000 description 1
- QWNUURXXBGFVRI-UHFFFAOYSA-N 6-acetamido-n-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]pyridine-3-carboxamide Chemical compound C1=NC(NC(=O)C)=CC=C1C(=O)NCCN1CCN(C=2N=CC=CC=2)CC1 QWNUURXXBGFVRI-UHFFFAOYSA-N 0.000 description 1
- RDELIIVICDCDCR-UHFFFAOYSA-N 6-amino-n-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]pyridine-3-carboxamide Chemical compound C1=NC(N)=CC=C1C(=O)NCCN1CCN(C=2N=CC=CC=2)CC1 RDELIIVICDCDCR-UHFFFAOYSA-N 0.000 description 1
- YXQHDGPNHAQAHS-UHFFFAOYSA-N 6-amino-n-[2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl]pyridine-3-carboxamide Chemical compound CC1=CC=NC(N2CCN(CCNC(=O)C=3C=NC(N)=CC=3)CC2)=C1 YXQHDGPNHAQAHS-UHFFFAOYSA-N 0.000 description 1
- SOIVMPKXYJINDF-UHFFFAOYSA-N 6-amino-n-[2-[4-(6-methoxypyridin-2-yl)piperazin-1-yl]ethyl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(N2CCN(CCNC(=O)C=3C=NC(N)=CC=3)CC2)=N1 SOIVMPKXYJINDF-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1487771 | 1971-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134986B true NO134986B (xx) | 1976-10-11 |
| NO134986C NO134986C (xx) | 1977-01-19 |
Family
ID=10049096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1707/72A NO134986C (xx) | 1971-05-14 | 1972-05-12 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3821225A (xx) |
| JP (1) | JPS5111635B1 (xx) |
| AT (1) | AT316561B (xx) |
| AU (1) | AU458800B2 (xx) |
| BE (1) | BE783420A (xx) |
| CA (1) | CA957374A (xx) |
| CH (1) | CH553198A (xx) |
| DK (1) | DK137757B (xx) |
| FR (1) | FR2137689B1 (xx) |
| GB (1) | GB1345449A (xx) |
| HU (1) | HU163334B (xx) |
| IE (1) | IE36441B1 (xx) |
| NL (1) | NL146500B (xx) |
| NO (1) | NO134986C (xx) |
| SE (1) | SE381468B (xx) |
| SU (1) | SU460624A3 (xx) |
| ZA (1) | ZA722735B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895846A (en) * | 1984-04-11 | 1990-01-23 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moieties |
| US4755512A (en) * | 1984-04-11 | 1988-07-05 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities |
| DE4425143A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Substituierte Pyrimidinverbindungen und deren Verwendung |
| AU2002226197B2 (en) * | 2001-01-30 | 2006-02-16 | Cytopia Pty Ltd | Methods of inhibiting kinases |
| CA2436487A1 (en) * | 2001-01-30 | 2002-08-08 | Cytopia Pty Ltd. | Methods of inhibiting kinases |
| US7176310B1 (en) | 2002-04-09 | 2007-02-13 | Ucb Sa | Pyrimidinecarboxamide derivatives and their use as anti-inflammatory agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1279843A (en) * | 1969-05-23 | 1972-06-28 | Science Union & Cie | Benzamidoethyl-piperazines and process for their preparation |
-
1971
- 1971-05-14 GB GB1487771*[A patent/GB1345449A/en not_active Expired
-
1972
- 1972-04-24 ZA ZA722735A patent/ZA722735B/xx unknown
- 1972-05-02 AU AU41763/72A patent/AU458800B2/en not_active Expired
- 1972-05-05 US US00250567A patent/US3821225A/en not_active Expired - Lifetime
- 1972-05-09 AT AT405672A patent/AT316561B/de not_active IP Right Cessation
- 1972-05-09 SE SE7206147A patent/SE381468B/xx unknown
- 1972-05-09 CH CH684172A patent/CH553198A/fr not_active IP Right Cessation
- 1972-05-10 FR FR7216617A patent/FR2137689B1/fr not_active Expired
- 1972-05-11 IE IE630/72A patent/IE36441B1/xx unknown
- 1972-05-11 CA CA142,220*7A patent/CA957374A/en not_active Expired
- 1972-05-12 NL NL727206392A patent/NL146500B/xx unknown
- 1972-05-12 DK DK237172AA patent/DK137757B/da unknown
- 1972-05-12 JP JP47046508A patent/JPS5111635B1/ja active Pending
- 1972-05-12 BE BE783420A patent/BE783420A/xx unknown
- 1972-05-12 NO NO1707/72A patent/NO134986C/no unknown
- 1972-05-12 SU SU1785482A patent/SU460624A3/ru active
- 1972-05-13 HU HUSI1264A patent/HU163334B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7206392A (xx) | 1972-11-16 |
| AT316561B (de) | 1974-07-25 |
| SE381468B (sv) | 1975-12-08 |
| CA957374A (en) | 1974-11-05 |
| GB1345449A (en) | 1974-01-30 |
| AU458800B2 (en) | 1975-03-06 |
| CH553198A (fr) | 1974-08-30 |
| HU163334B (xx) | 1973-07-28 |
| DK137757B (da) | 1978-05-01 |
| DK137757C (xx) | 1978-10-02 |
| DE2222934A1 (de) | 1972-11-30 |
| FR2137689A1 (xx) | 1972-12-29 |
| IE36441L (en) | 1972-11-14 |
| DE2222934B2 (de) | 1976-08-26 |
| SU460624A3 (ru) | 1975-02-15 |
| AU4176372A (en) | 1973-11-08 |
| FR2137689B1 (xx) | 1975-10-31 |
| NO134986C (xx) | 1977-01-19 |
| JPS5111635B1 (xx) | 1976-04-13 |
| NL146500B (nl) | 1975-07-15 |
| US3821225A (en) | 1974-06-28 |
| IE36441B1 (en) | 1976-11-10 |
| ZA722735B (en) | 1973-05-30 |
| BE783420A (fr) | 1972-11-13 |
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