CS218553B2 - Method of making the alkylesters of the substituted 5-phenylsulfinyl-2-benzimidazolcarbam acid - Google Patents
Method of making the alkylesters of the substituted 5-phenylsulfinyl-2-benzimidazolcarbam acid Download PDFInfo
- Publication number
- CS218553B2 CS218553B2 CS744656A CS465674A CS218553B2 CS 218553 B2 CS218553 B2 CS 218553B2 CS 744656 A CS744656 A CS 744656A CS 465674 A CS465674 A CS 465674A CS 218553 B2 CS218553 B2 CS 218553B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- phenylsulfinyl
- substituted
- formula
- alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 title description 4
- 125000005907 alkyl ester group Chemical group 0.000 title description 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- GUVHJRKHTWAPJG-UHFFFAOYSA-N [6-(benzenesulfinyl)-1h-benzimidazol-2-yl]carbamic acid Chemical class C=1C=C2NC(NC(=O)O)=NC2=CC=1S(=O)C1=CC=CC=C1 GUVHJRKHTWAPJG-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- -1 alkyl chloroformate Chemical compound 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003826 tablet 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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- YLEPPBFOGUYOEI-UHFFFAOYSA-N 4-phenylsulfanylbenzene-1,2-diamine Chemical class C1=C(N)C(N)=CC=C1SC1=CC=CC=C1 YLEPPBFOGUYOEI-UHFFFAOYSA-N 0.000 description 1
- SILINCSPXIUHQG-UHFFFAOYSA-N CC(C)OC(=O)NC1=NC2=C(N1)C=C(C=C2)S(=O)C3=C(C=CC(=C3)Cl)Cl Chemical compound CC(C)OC(=O)NC1=NC2=C(N1)C=C(C=C2)S(=O)C3=C(C=CC(=C3)Cl)Cl SILINCSPXIUHQG-UHFFFAOYSA-N 0.000 description 1
- ZRILIWQKUUQEEG-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)S(=O)C2=CC3=C(C=C2)N=C(N3)NC(=O)OC(C)C Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)S(=O)C2=CC3=C(C=C2)N=C(N3)NC(=O)OC(C)C ZRILIWQKUUQEEG-UHFFFAOYSA-N 0.000 description 1
- SODDYWWIYANVBM-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC SODDYWWIYANVBM-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241000251556 Chordata Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 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
- 241001547406 Hyostrongylus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001126263 Strongylidae Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- 230000002496 gastric effect Effects 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
- 244000000013 helminth Species 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 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
- ZUYPRQOUYRVNNK-UHFFFAOYSA-N methyl N-[6-(2,5-dichlorophenyl)sulfinyl-1H-benzimidazol-2-yl]carbamate Chemical compound COC(NC=1NC2=C(N1)C=CC(=C2)S(=O)C2=C(C=CC(=C2)Cl)Cl)=O ZUYPRQOUYRVNNK-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 244000045947 parasite Species 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
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000600 sorbitol Substances 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
- 238000003756 stirring Methods 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
- 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| CS218553B2 true CS218553B2 (en) | 1983-02-25 |
Family
ID=5886239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS744656A CS218553B2 (en) | 1973-07-07 | 1974-07-02 | Method of making the alkylesters of the substituted 5-phenylsulfinyl-2-benzimidazolcarbam acid |
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 |
|---|---|
| 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 |
| JPS5840547B2 (ja) | 1983-09-06 |
| 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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