NO783086L - Fremgangsmaate for fremstilling av nye pyrimidinderivater - Google Patents
Fremgangsmaate for fremstilling av nye pyrimidinderivaterInfo
- Publication number
- NO783086L NO783086L NO783086A NO783086A NO783086L NO 783086 L NO783086 L NO 783086L NO 783086 A NO783086 A NO 783086A NO 783086 A NO783086 A NO 783086A NO 783086 L NO783086 L NO 783086L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- pyrimidine
- hydrogen
- lower alkyl
- pyrazolo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 10
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 methylethyl Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Chemical group 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OSUQULRSOJLDFU-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(C)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(C)NC(=S)N21 OSUQULRSOJLDFU-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- AVFLNALVPBLGEV-UHFFFAOYSA-N 4-chloro-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C2N(C)N=CC2=C1Cl AVFLNALVPBLGEV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- AMZCQXCAQVKYKZ-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(C(C)C)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(C(C)C)NC(=S)N21 AMZCQXCAQVKYKZ-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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MEUSJJFWVKBUFP-UHFFFAOYSA-N ethyl 5-amino-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1N MEUSJJFWVKBUFP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XYRVLCQVOLFELO-UHFFFAOYSA-N 1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CNC(=O)C2=C1N(C(C)C)N=C2 XYRVLCQVOLFELO-UHFFFAOYSA-N 0.000 description 2
- DTBUPNKKMFYZBZ-UHFFFAOYSA-N 3,10-dimethyl-3,4,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1,8,11-trien-5-one Chemical compound C1N=C2N(C)N=CC2=C2N(C)NC(=O)N21 DTBUPNKKMFYZBZ-UHFFFAOYSA-N 0.000 description 2
- SISQSWFOHNJVLP-UHFFFAOYSA-N 4-chloro-3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C(Cl)C2=C(C(C)C)NN=C21 SISQSWFOHNJVLP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AUBRWJZCZQAWIQ-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(CCCC)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(CCCC)NC(=S)N21 AUBRWJZCZQAWIQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- CDJQIJFWTUEUFF-UHFFFAOYSA-N chembl1401275 Chemical compound N1=CNC(=O)C2=C1N(C)N=C2 CDJQIJFWTUEUFF-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DPTRSSOWVXIMQM-UHFFFAOYSA-N ethyl 3-amino-5-propan-2-yl-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C1=C(N)NN=C1C(C)C DPTRSSOWVXIMQM-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- FIXCDCJILXZLJL-UHFFFAOYSA-N 1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)-2-propan-2-ylhydrazine Chemical compound CC(C)NNC1=NC=NC2=C1C=NN2C FIXCDCJILXZLJL-UHFFFAOYSA-N 0.000 description 1
- RVYSDXZMMQWFRL-UHFFFAOYSA-N 1-butyl-1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Chemical compound CCCCN(N)C1=NC=NC2=C1C=NN2C RVYSDXZMMQWFRL-UHFFFAOYSA-N 0.000 description 1
- DCTBMFDEKIMGLY-UHFFFAOYSA-N 1-methyl-1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Chemical compound CN(N)C1=NC=NC2=C1C=NN2C DCTBMFDEKIMGLY-UHFFFAOYSA-N 0.000 description 1
- BAIFEGFLPYIENO-UHFFFAOYSA-N 1-methyl-1-(1-propan-2-ylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Chemical compound N1=CN=C2N(C(C)C)N=CC2=C1N(C)N BAIFEGFLPYIENO-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FWXQHGCPQVZGDJ-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione Chemical compound C1=CN=CN2C(=S)NN=C21 FWXQHGCPQVZGDJ-UHFFFAOYSA-N 0.000 description 1
- VMXWGNGBYAOJAN-UHFFFAOYSA-N 3,4,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,7,11-tetraene-5-thione Chemical class N1=CN2C(S)=NN=C2C2=C1NN=C2 VMXWGNGBYAOJAN-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/833,103 US4124764A (en) | 1976-04-21 | 1977-09-13 | Meso-ionic didehydro derivatives of 1,7-dehydro-1-substituted-3H-pyrazolo[4,]-1,2,4-triazolo[4,3-c]pyrimidine-3-thiones and 3-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783086L true NO783086L (no) | 1979-03-14 |
Family
ID=25263436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783086A NO783086L (no) | 1977-09-13 | 1978-09-12 | Fremgangsmaate for fremstilling av nye pyrimidinderivater |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5452098A (it) |
| AU (1) | AU3914178A (it) |
| BE (1) | BE870456A (it) |
| CA (1) | CA1095907A (it) |
| DE (1) | DE2838029A1 (it) |
| DK (1) | DK402178A (it) |
| FR (1) | FR2402658A1 (it) |
| GB (1) | GB2004278B (it) |
| HU (1) | HU176023B (it) |
| IT (1) | IT1099031B (it) |
| NL (1) | NL7809035A (it) |
| NO (1) | NO783086L (it) |
| SE (1) | SE7809601L (it) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053474A (en) * | 1976-04-21 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine |
-
1978
- 1978-08-18 CA CA309,665A patent/CA1095907A/en not_active Expired
- 1978-08-22 AU AU39141/78A patent/AU3914178A/en active Pending
- 1978-08-31 DE DE19782838029 patent/DE2838029A1/de not_active Withdrawn
- 1978-09-04 NL NL7809035A patent/NL7809035A/xx not_active Application Discontinuation
- 1978-09-11 HU HU78SU991A patent/HU176023B/hu unknown
- 1978-09-11 FR FR7826046A patent/FR2402658A1/fr not_active Withdrawn
- 1978-09-12 IT IT27559/78A patent/IT1099031B/it active
- 1978-09-12 DK DK402178A patent/DK402178A/da unknown
- 1978-09-12 GB GB7836516A patent/GB2004278B/en not_active Expired
- 1978-09-12 NO NO783086A patent/NO783086L/no unknown
- 1978-09-12 SE SE7809601A patent/SE7809601L/xx unknown
- 1978-09-13 BE BE190466A patent/BE870456A/xx unknown
- 1978-09-13 JP JP11321978A patent/JPS5452098A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2838029A1 (de) | 1979-03-22 |
| BE870456A (fr) | 1979-03-13 |
| AU3914178A (en) | 1980-02-28 |
| IT1099031B (it) | 1985-09-18 |
| GB2004278A (en) | 1979-03-28 |
| GB2004278B (en) | 1982-01-13 |
| IT7827559A0 (it) | 1978-09-12 |
| NL7809035A (nl) | 1979-03-15 |
| CA1095907A (en) | 1981-02-17 |
| JPS5452098A (en) | 1979-04-24 |
| HU176023B (en) | 1980-11-28 |
| FR2402658A1 (fr) | 1979-04-06 |
| SE7809601L (sv) | 1979-03-14 |
| DK402178A (da) | 1979-03-14 |
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