JPS5840547B2 - ５− フエニルスルフイニル −２− ベンズイミダゾ−ル − カルバミンサンエステルノセイホウ - Google Patents
５− フエニルスルフイニル −２− ベンズイミダゾ−ル − カルバミンサンエステルノセイホウInfo
- Publication number
- JPS5840547B2 JPS5840547B2 JP49076915A JP7691574A JPS5840547B2 JP S5840547 B2 JPS5840547 B2 JP S5840547B2 JP 49076915 A JP49076915 A JP 49076915A JP 7691574 A JP7691574 A JP 7691574A JP S5840547 B2 JPS5840547 B2 JP S5840547B2
- Authority
- JP
- Japan
- Prior art keywords
- carbamic acid
- phenylsulfinyl
- benzimidazolyl
- ester
- phenylthio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- -1 nibutyl Chemical group 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 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
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- UOYJDZRXRJVTTM-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC(C)C Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC(C)C UOYJDZRXRJVTTM-UHFFFAOYSA-N 0.000 description 1
- BAWBYJWZCRETDM-UHFFFAOYSA-N COC(=O)NC1=NC2=CC=C(C=C2N1)S(=O)C1=CC=C(C)C=C1 Chemical compound COC(=O)NC1=NC2=CC=C(C=C2N1)S(=O)C1=CC=C(C)C=C1 BAWBYJWZCRETDM-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000102542 Kara Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000555736 Sciurus vulgaris Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GUVHJRKHTWAPJG-UHFFFAOYSA-N [6-(benzenesulfinyl)-1h-benzimidazol-2-yl]carbamic acid Chemical compound C=1C=C2NC(NC(=O)O)=NC2=CC=1S(=O)C1=CC=CC=C1 GUVHJRKHTWAPJG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HDDSHPAODJUKPD-UHFFFAOYSA-N fenbendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 HDDSHPAODJUKPD-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HFKRLWIJFAUNAW-UHFFFAOYSA-N methyl N-[6-(2,5-dichlorophenyl)sulfanyl-1H-benzimidazol-2-yl]carbamate Chemical compound COC(NC=1NC2=C(N1)C=CC(=C2)SC2=C(C=CC(=C2)Cl)Cl)=O HFKRLWIJFAUNAW-UHFFFAOYSA-N 0.000 description 1
- ZFAYUNVSPNUTQP-UHFFFAOYSA-N methyl N-[6-(3-methylphenyl)sulfinyl-1H-benzimidazol-2-yl]carbamate Chemical compound CC=1C=C(C=CC1)S(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1 ZFAYUNVSPNUTQP-UHFFFAOYSA-N 0.000 description 1
- YPYUTEHWDGASPN-UHFFFAOYSA-N methyl n-[6-(4-chlorophenyl)sulfanyl-1h-benzimidazol-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=C(Cl)C=C1 YPYUTEHWDGASPN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LOVDFESMGBQIDH-UHFFFAOYSA-N propan-2-yl N-[6-(2,5-dichlorophenyl)sulfanyl-1H-benzimidazol-2-yl]carbamate Chemical compound C(C)(C)OC(NC=1NC2=C(N1)C=CC(=C2)SC2=C(C=CC(=C2)Cl)Cl)=O LOVDFESMGBQIDH-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334631 DE2334631A1 (de) | 1973-07-07 | 1973-07-07 | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5040567A JPS5040567A (en, 2012) | 1975-04-14 |
| JPS5840547B2 true JPS5840547B2 (ja) | 1983-09-06 |
Family
ID=5886239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49076915A Expired JPS5840547B2 (ja) | 1973-07-07 | 1974-07-06 | ５− フエニルスルフイニル −２− ベンズイミダゾ−ル − カルバミンサンエステルノセイホウ |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5840547B2 (en, 2012) |
| AT (1) | AT337201B (en, 2012) |
| BE (1) | BE817364A (en, 2012) |
| CA (1) | CA1030970A (en, 2012) |
| CH (1) | CH605821A5 (en, 2012) |
| CS (1) | CS218553B2 (en, 2012) |
| DD (1) | DD114262A5 (en, 2012) |
| DE (1) | DE2334631A1 (en, 2012) |
| DK (1) | DK362674A (en, 2012) |
| EG (1) | EG11414A (en, 2012) |
| ES (1) | ES427869A1 (en, 2012) |
| FI (1) | FI60202C (en, 2012) |
| FR (1) | FR2235688B1 (en, 2012) |
| GB (1) | GB1428933A (en, 2012) |
| HK (1) | HK8180A (en, 2012) |
| IL (1) | IL45189A (en, 2012) |
| IT (1) | IT1050720B (en, 2012) |
| MY (1) | MY8000272A (en, 2012) |
| NL (1) | NL7408945A (en, 2012) |
| NO (1) | NO141758C (en, 2012) |
| SE (1) | SE7408868L (en, 2012) |
| ZA (1) | ZA744335B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1107749B (it) * | 1977-10-06 | 1985-11-25 | Montedison Spa | Benzimidazolcarbammato particolarmente attivo contro i parassiti gastroenterici e polmonari |
| DD147539A5 (de) * | 1978-12-06 | 1981-04-08 | Montedison Spa | Herstellung von in 5(6)-stellung substituierten benzimidazol-carbamaten |
| DE3719783A1 (de) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung von 5-phenylsulfinyl-1h-2-(methoxycarbonylamino)- benzimidazol |
| CN102863392A (zh) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | 一种奥芬达唑生产过程中大幅减少溶剂使用量的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
-
1973
- 1973-07-07 DE DE19732334631 patent/DE2334631A1/de not_active Ceased
-
1974
- 1974-06-28 GB GB2879374A patent/GB1428933A/en not_active Expired
- 1974-07-02 NL NL7408945A patent/NL7408945A/xx not_active Application Discontinuation
- 1974-07-02 CS CS744656A patent/CS218553B2/cs unknown
- 1974-07-02 ES ES427869A patent/ES427869A1/es not_active Expired
- 1974-07-03 IL IL45189A patent/IL45189A/en unknown
- 1974-07-03 CH CH911374A patent/CH605821A5/xx not_active IP Right Cessation
- 1974-07-03 CA CA203,893A patent/CA1030970A/en not_active Expired
- 1974-07-04 DD DD179700A patent/DD114262A5/xx unknown
- 1974-07-04 FI FI2052/74A patent/FI60202C/fi active
- 1974-07-05 AT AT555674A patent/AT337201B/de not_active IP Right Cessation
- 1974-07-05 IT IT24889/74A patent/IT1050720B/it active
- 1974-07-05 NO NO742457A patent/NO141758C/no unknown
- 1974-07-05 FR FR7423523A patent/FR2235688B1/fr not_active Expired
- 1974-07-05 SE SE7408868A patent/SE7408868L/xx not_active Application Discontinuation
- 1974-07-05 ZA ZA00744335A patent/ZA744335B/xx unknown
- 1974-07-05 DK DK362674A patent/DK362674A/da unknown
- 1974-07-06 JP JP49076915A patent/JPS5840547B2/ja not_active Expired
- 1974-07-06 EG EG259/74A patent/EG11414A/xx active
- 1974-07-08 BE BE146318A patent/BE817364A/xx not_active IP Right Cessation
-
1980
- 1980-03-06 HK HK81/80A patent/HK8180A/xx unknown
- 1980-12-30 MY MY272/80A patent/MY8000272A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS218553B2 (en) | 1983-02-25 |
| ZA744335B (en) | 1975-07-30 |
| JPS5040567A (en, 2012) | 1975-04-14 |
| IL45189A (en) | 1977-03-31 |
| FI60202B (fi) | 1981-08-31 |
| NO742457L (en, 2012) | 1975-02-03 |
| NL7408945A (nl) | 1975-01-09 |
| EG11414A (en) | 1977-02-28 |
| IL45189A0 (en) | 1974-10-22 |
| SE7408868L (en, 2012) | 1975-01-08 |
| NO141758C (no) | 1980-05-07 |
| DE2334631A1 (de) | 1975-03-27 |
| DD114262A5 (en, 2012) | 1975-07-20 |
| FR2235688A1 (en, 2012) | 1975-01-31 |
| GB1428933A (en) | 1976-03-24 |
| HK8180A (en) | 1980-03-14 |
| AU7089974A (en) | 1976-01-08 |
| FR2235688B1 (en, 2012) | 1978-07-28 |
| IT1050720B (it) | 1981-03-20 |
| ES427869A1 (es) | 1976-12-16 |
| FI60202C (fi) | 1981-12-10 |
| BE817364A (fr) | 1975-01-08 |
| FI205274A7 (en, 2012) | 1975-01-08 |
| CH605821A5 (en, 2012) | 1978-10-13 |
| CA1030970A (en) | 1978-05-09 |
| ATA555674A (de) | 1976-10-15 |
| MY8000272A (en) | 1980-12-31 |
| AT337201B (de) | 1977-06-27 |
| DK362674A (en, 2012) | 1975-03-17 |
| NO141758B (no) | 1980-01-28 |
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