IE43102B1 - Process for preparing a methyl-isoxazolyl compound - Google Patents
Process for preparing a methyl-isoxazolyl compoundInfo
- Publication number
- IE43102B1 IE43102B1 IE947/76A IE94776A IE43102B1 IE 43102 B1 IE43102 B1 IE 43102B1 IE 947/76 A IE947/76 A IE 947/76A IE 94776 A IE94776 A IE 94776A IE 43102 B1 IE43102 B1 IE 43102B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- process according
- methyl
- carried out
- temperature
- Prior art date
Links
- -1 methyl-isoxazolyl compound Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 230000020477 pH reduction Effects 0.000 claims description 11
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012022 methylating agents Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- 230000011987 methylation Effects 0.000 claims description 5
- 238000007069 methylation reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 3
- 238000012986 modification Methods 0.000 claims 3
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 abstract description 2
- OILSIQIYOURQEA-UHFFFAOYSA-N 1-[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]propan-2-one Chemical compound CC(=O)CC1=NOC(C=2NSC3=CC=CC=C3C=2O)=N1 OILSIQIYOURQEA-UHFFFAOYSA-N 0.000 abstract 1
- OCEZJTJAJHRHDA-UHFFFAOYSA-N n-(5-methyl-1,2-oxazol-3-yl)-2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)CN2S(C3=CC=CC=C3C2=O)(=O)=O)=N1 OCEZJTJAJHRHDA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000012431 aqueous reaction media Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- XBQPBEPIWBCCPQ-UHFFFAOYSA-N 1-[5-(4-hydroxy-2-methyl-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]propan-2-one Chemical compound CN1SC2=CC=CC=C2C(O)=C1C1=NC(CC(C)=O)=NO1 XBQPBEPIWBCCPQ-UHFFFAOYSA-N 0.000 description 1
- JWINJBQCXAHJFH-UHFFFAOYSA-N 2h-1,2-benzothiazine;oxadiazole Chemical class C1=CON=N1.C1=CC=C2C=CNSC2=C1 JWINJBQCXAHJFH-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 101150053844 APP1 gene Proteins 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- 101100189105 Homo sapiens PABPC4 gene Proteins 0.000 description 1
- 206010020843 Hyperthermia Diseases 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
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 102100039424 Polyadenylate-binding protein 4 Human genes 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KNYFJYVFUYERQR-UHFFFAOYSA-N methyl 2-(3-oxo-1,2-benzothiazol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OC)SC2=C1 KNYFJYVFUYERQR-UHFFFAOYSA-N 0.000 description 1
- GEUURTZIEGFZAG-UHFFFAOYSA-N methyl 4-hydroxy-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)NC(C(=O)OC)=C(O)C2=C1 GEUURTZIEGFZAG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000003981 vehicle Substances 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE336/78A IE43103B1 (en) | 1975-05-21 | 1976-05-04 | Benzothiazine 1,1,-dioxide derivatives |
| IE337/78A IE43104B1 (en) | 1975-05-21 | 1976-05-04 | 3-oxo-1,2-benzisothiazole derivative and the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/577,568 US3957772A (en) | 1975-05-21 | 1975-05-21 | Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2h-1,2-benzothiazine 1,1-dioxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43102L IE43102L (en) | 1976-11-21 |
| IE43102B1 true IE43102B1 (en) | 1980-12-17 |
Family
ID=24309281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE947/76A IE43102B1 (en) | 1975-05-21 | 1976-05-04 | Process for preparing a methyl-isoxazolyl compound |
Country Status (10)
| Country | Link |
|---|---|
| CH (1) | CH629802A5 (nl) |
| DK (3) | DK148479C (nl) |
| ES (1) | ES448088A1 (nl) |
| FI (1) | FI63230C (nl) |
| IE (1) | IE43102B1 (nl) |
| IN (1) | IN143577B (nl) |
| MX (1) | MX3139E (nl) |
| NO (1) | NO145917C (nl) |
| PH (2) | PH14848A (nl) |
| SE (2) | SE429043B (nl) |
-
1976
- 1976-03-30 IN IN548/CAL/76A patent/IN143577B/en unknown
- 1976-05-04 IE IE947/76A patent/IE43102B1/en unknown
- 1976-05-10 MX MX000219U patent/MX3139E/es unknown
- 1976-05-17 PH PH18443A patent/PH14848A/en unknown
- 1976-05-19 DK DK219876A patent/DK148479C/da active
- 1976-05-20 NO NO761724A patent/NO145917C/no unknown
- 1976-05-20 ES ES448088A patent/ES448088A1/es not_active Expired
- 1976-05-20 FI FI761431A patent/FI63230C/fi not_active IP Right Cessation
- 1976-05-20 SE SE7605752A patent/SE429043B/xx not_active IP Right Cessation
- 1976-05-21 CH CH642776A patent/CH629802A5/de not_active IP Right Cessation
-
1980
- 1980-01-22 DK DK25180A patent/DK149752C/da not_active IP Right Cessation
- 1980-01-22 DK DK25280A patent/DK148478C/da active
- 1980-03-03 SE SE8001649A patent/SE447112B/sv not_active IP Right Cessation
-
1981
- 1981-01-28 PH PH25141A patent/PH16804A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI63230C (fi) | 1983-05-10 |
| IN143577B (nl) | 1977-12-31 |
| SE8001649L (sv) | 1980-03-03 |
| SE447112B (sv) | 1986-10-27 |
| MX3139E (es) | 1980-05-06 |
| NO145917B (no) | 1982-03-15 |
| SE429043B (sv) | 1983-08-08 |
| CH629802A5 (en) | 1982-05-14 |
| PH14848A (en) | 1982-01-06 |
| NO145917C (no) | 1982-06-23 |
| NO761724L (nl) | 1976-11-23 |
| FI63230B (fi) | 1983-01-31 |
| DK149752B (da) | 1986-09-22 |
| DK148479C (da) | 1985-12-16 |
| DK25180A (da) | 1980-01-22 |
| FI761431A (nl) | 1976-11-22 |
| DK148478C (da) | 1985-12-16 |
| DK25280A (da) | 1980-01-22 |
| DK149752C (da) | 1987-03-16 |
| IE43102L (en) | 1976-11-21 |
| DK148479B (da) | 1985-07-15 |
| DK148478B (da) | 1985-07-15 |
| SE7605752L (sv) | 1976-11-22 |
| DK219876A (da) | 1976-11-22 |
| PH16804A (en) | 1984-03-01 |
| ES448088A1 (es) | 1977-07-01 |
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