FI59406C - Foerfarande foer framstaellning av substituerade 2h-pyran-2,6(3h)-dionderivat vilka inhiberar antigen-antikroppreaktioner - Google Patents
Foerfarande foer framstaellning av substituerade 2h-pyran-2,6(3h)-dionderivat vilka inhiberar antigen-antikroppreaktioner Download PDFInfo
- Publication number
- FI59406C FI59406C FI752139A FI752139A FI59406C FI 59406 C FI59406 C FI 59406C FI 752139 A FI752139 A FI 752139A FI 752139 A FI752139 A FI 752139A FI 59406 C FI59406 C FI 59406C
- Authority
- FI
- Finland
- Prior art keywords
- pyran
- dione
- acetyl
- hydroxy
- ethylidene
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- 239000000126 substance Substances 0.000 title description 3
- 210000002268 wool Anatomy 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- -1 carbamoyloxyphenyl Chemical group 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000203 mixture Substances 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- ISDVKWGLGFGXJD-UHFFFAOYSA-N chembl3248291 Chemical compound CC(=O)C1=C(O)OC(=O)C(C(C)=O)=C1O ISDVKWGLGFGXJD-UHFFFAOYSA-N 0.000 description 9
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical class O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 239000008024 pharmaceutical diluent Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VRXLPSVAKDQLPT-UHFFFAOYSA-N (4-aminophenyl) carbamate;hydrochloride Chemical compound Cl.NC(=O)OC1=CC=C(N)C=C1 VRXLPSVAKDQLPT-UHFFFAOYSA-N 0.000 description 1
- XVCKCCODMHCXJD-UHFFFAOYSA-N (4-aminophenyl)urea Chemical compound NC(=O)NC1=CC=C(N)C=C1 XVCKCCODMHCXJD-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- YWLVUWDYMMCFNI-UHFFFAOYSA-N 3-acetyl-4-hydroxy-5-[1-(propylamino)ethylidene]pyran-2,6-dione Chemical compound CCCNC(C)=C1C(=O)OC(=O)C(C(C)=O)=C1O YWLVUWDYMMCFNI-UHFFFAOYSA-N 0.000 description 1
- GJIOTVJBYVBQCB-UHFFFAOYSA-N 3-acetyl-5-[1-(4-aminoanilino)ethylidene]-4-hydroxypyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1=C(C)NC1=CC=C(N)C=C1 GJIOTVJBYVBQCB-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- PBYHDPMCTNZGGK-UHFFFAOYSA-N CC(C(C(OC(C1=CCNC2(C=CC=CC2)O)=O)=O)=C1O)=O Chemical compound CC(C(C(OC(C1=CCNC2(C=CC=CC2)O)=O)=O)=C1O)=O PBYHDPMCTNZGGK-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- SADOVKWYGCAFGV-UHFFFAOYSA-N [4-[1-(5-acetyl-4,6-dihydroxy-2-oxopyran-3-yl)ethylideneamino]phenyl] carbamate Chemical compound CC(=NC1=CC=C(C=C1)OC(=O)N)C2=C(C(=C(OC2=O)O)C(=O)C)O SADOVKWYGCAFGV-UHFFFAOYSA-N 0.000 description 1
- CEODFOCUYIVIRJ-UHFFFAOYSA-N [4-[1-(5-acetyl-4,6-dihydroxy-2-oxopyran-3-yl)ethylideneamino]phenyl]urea Chemical compound CC(=NC1=CC=C(C=C1)NC(=O)N)C2=C(C(=C(OC2=O)O)C(=O)C)O CEODFOCUYIVIRJ-UHFFFAOYSA-N 0.000 description 1
- HONUUMVBUYWSJR-UHFFFAOYSA-N [4-[1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethylamino]phenyl] n-benzylcarbamate Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1=C(C)NC(C=C1)=CC=C1OC(=O)NCC1=CC=CC=C1 HONUUMVBUYWSJR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012866 crystallographic experiment Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000007332 vesicle formation Effects 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49264074A | 1974-07-29 | 1974-07-29 | |
| US49264074 | 1974-07-29 | ||
| US57089675A | 1975-04-23 | 1975-04-23 | |
| US57089675 | 1975-04-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752139A7 FI752139A7 (enrdf_load_stackoverflow) | 1976-01-30 |
| FI59406B FI59406B (fi) | 1981-04-30 |
| FI59406C true FI59406C (fi) | 1981-08-10 |
Family
ID=27050812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752139A FI59406C (fi) | 1974-07-29 | 1975-07-24 | Foerfarande foer framstaellning av substituerade 2h-pyran-2,6(3h)-dionderivat vilka inhiberar antigen-antikroppreaktioner |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1572271A (en) * | 1976-06-16 | 1980-07-30 | Smithkline Corp | 5-acetyl-4-hydroxy-(3(1-phenylaminoethylidene)-2h-pyran-2,6(3h)-dione derivatives |
| FR2388808A1 (fr) * | 1977-04-29 | 1978-11-24 | Smithkline Corp | Derives substitues de 2h-pyranne-2,6(3h)-diones, leur preparation et leur application en therapeutique |
| US4160021A (en) * | 1977-05-23 | 1979-07-03 | Smithkline Corporation | Substituted 2H-pyran-2,6(3H)-dione derivatives |
| US5263435A (en) * | 1992-08-12 | 1993-11-23 | Mitsuba Electric Manufacturing Co., Ltd. | Volute horn and method of manufacturing |
-
1975
- 1975-07-22 DK DK332675AA patent/DK134552B/da not_active IP Right Cessation
- 1975-07-22 CA CA231,964A patent/CA1064509A/en not_active Expired
- 1975-07-23 ES ES439664A patent/ES439664A1/es not_active Expired
- 1975-07-24 HU HU75SI1481A patent/HU174067B/hu unknown
- 1975-07-24 IE IE1663/75A patent/IE41709B1/en unknown
- 1975-07-24 FI FI752139A patent/FI59406C/fi not_active IP Right Cessation
- 1975-07-24 IL IL47792A patent/IL47792A/xx unknown
- 1975-07-24 GB GB30936/75A patent/GB1521712A/en not_active Expired
- 1975-07-25 FR FR7523296A patent/FR2280367A1/fr active Granted
- 1975-07-25 LU LU73066A patent/LU73066A1/xx unknown
- 1975-07-25 NO NO752638A patent/NO142668C/no unknown
- 1975-07-28 AT AT584475A patent/AT343657B/de not_active IP Right Cessation
- 1975-07-28 CH CH982875A patent/CH615433A5/de not_active IP Right Cessation
- 1975-07-29 DD DD187549A patent/DD118626A5/xx unknown
- 1975-07-29 JP JP50092974A patent/JPS5136458A/ja active Pending
- 1975-07-29 DE DE2533843A patent/DE2533843C2/de not_active Expired
- 1975-07-29 NL NL7509032A patent/NL7509032A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE41709B1 (en) | 1980-03-12 |
| JPS5136458A (en) | 1976-03-27 |
| ATA584475A (de) | 1977-10-15 |
| FI59406B (fi) | 1981-04-30 |
| FR2280367A1 (fr) | 1976-02-27 |
| CA1064509A (en) | 1979-10-16 |
| ES439664A1 (es) | 1977-03-01 |
| NO142668B (no) | 1980-06-16 |
| AU8345075A (en) | 1977-02-03 |
| NO142668C (no) | 1980-09-24 |
| DE2533843C2 (de) | 1984-06-14 |
| NO752638L (enrdf_load_stackoverflow) | 1976-01-30 |
| IL47792A0 (en) | 1975-10-15 |
| FI752139A7 (enrdf_load_stackoverflow) | 1976-01-30 |
| NL7509032A (nl) | 1976-02-02 |
| LU73066A1 (enrdf_load_stackoverflow) | 1976-03-02 |
| DK332675A (enrdf_load_stackoverflow) | 1976-01-30 |
| IL47792A (en) | 1978-06-15 |
| AT343657B (de) | 1978-06-12 |
| DK134552B (da) | 1976-11-29 |
| DE2533843A1 (de) | 1976-02-19 |
| IE41709L (en) | 1976-01-29 |
| DK134552C (enrdf_load_stackoverflow) | 1977-05-09 |
| CH615433A5 (en) | 1980-01-31 |
| HU174067B (hu) | 1979-10-28 |
| DD118626A5 (enrdf_load_stackoverflow) | 1976-03-12 |
| FR2280367B1 (enrdf_load_stackoverflow) | 1979-08-10 |
| GB1521712A (en) | 1978-08-16 |
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