NO117369B - - Google Patents
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- Publication number
- NO117369B NO117369B NO65158028A NO15802865A NO117369B NO 117369 B NO117369 B NO 117369B NO 65158028 A NO65158028 A NO 65158028A NO 15802865 A NO15802865 A NO 15802865A NO 117369 B NO117369 B NO 117369B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- compound
- acid
- imidazo
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 18
- -1 aminophenyl Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical group N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 230000007306 turnover Effects 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000001816 cooling Methods 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 210000003608 fece Anatomy 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001494479 Pecora Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 150000003557 thiazoles Chemical class 0.000 description 5
- 241000283690 Bos taurus Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 230000000507 anthelmentic effect Effects 0.000 description 4
- 235000013330 chicken meat Nutrition 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical class C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- VSPWNWLVZSICCK-UHFFFAOYSA-N 6-thiophen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole;hydrochloride Chemical compound Cl.N1=C2SC=CN2CC1C1=CC=CS1 VSPWNWLVZSICCK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TWOQVRDPCSGVLB-UHFFFAOYSA-N n-[3-(2-hydroxy-2-thiophen-2-ylethyl)-1,3-thiazol-2-ylidene]acetamide Chemical compound CC(=O)N=C1SC=CN1CC(O)C1=CC=CS1 TWOQVRDPCSGVLB-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- KJVRURZDIOVSSQ-UHFFFAOYSA-N 2-bromo-1-(3-chlorophenyl)ethanone Chemical compound ClC1=CC=CC(C(=O)CBr)=C1 KJVRURZDIOVSSQ-UHFFFAOYSA-N 0.000 description 2
- 241000204725 Ascaridia galli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241001147667 Dictyocaulus Species 0.000 description 2
- 241000180412 Dictyocaulus filaria Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000920462 Heterakis Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- LKEDFUGOJINPBB-UHFFFAOYSA-N N-[3-[2-(3-bromophenyl)-2-oxoethyl]-1,3-thiazolidin-2-ylidene]acetamide hydrochloride Chemical compound Cl.C(C)(=O)N=C1SCCN1CC(C1=CC(=CC=C1)Br)=O LKEDFUGOJINPBB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- JTWVMLYUUYVAMZ-UHFFFAOYSA-N [Br-].NC=1SC=C[N+]=1CC(C1=CC=C(C=C1)F)=O Chemical compound [Br-].NC=1SC=C[N+]=1CC(C1=CC=C(C=C1)F)=O JTWVMLYUUYVAMZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 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
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZLLINCGFXANOHY-UHFFFAOYSA-N oxalic acid;6-thiophen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound OC(=O)C(O)=O.N1=C2SC=CN2CC1C1=CC=CS1 ZLLINCGFXANOHY-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- LQQKDSXCDXHLLF-UHFFFAOYSA-N 1,3-dibromopropan-2-one Chemical class BrCC(=O)CBr LQQKDSXCDXHLLF-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- VJVCQKOMUMNIGE-UHFFFAOYSA-N 1,3-thiazolidin-2-amine Chemical compound NC1NCCS1 VJVCQKOMUMNIGE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SIVCPATXICONBJ-UHFFFAOYSA-N 1-(3-bromophenyl)-2-(2-imino-1,3-thiazolidin-3-yl)ethanone Chemical compound BrC1=CC=CC(C(=O)CN2C(SCC2)=N)=C1 SIVCPATXICONBJ-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QGWIXYPZHNXEFW-UHFFFAOYSA-N 6-thiophen-2-yl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;hydrochloride Chemical compound Cl.N1=C2SCCN2CC1C1=CC=CS1 QGWIXYPZHNXEFW-UHFFFAOYSA-N 0.000 description 1
- RFOLEEQBNNSICL-UHFFFAOYSA-N 6-thiophen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC=CN2CC1C1=CC=CS1 RFOLEEQBNNSICL-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 241000220438 Arachis Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GFPHIFDMORLNHI-UHFFFAOYSA-N Br.N=C1SCCN1CC(C1=CC(=CC=C1)Br)=O Chemical compound Br.N=C1SCCN1CC(C1=CC(=CC=C1)Br)=O GFPHIFDMORLNHI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000931177 Bunostomum trigonocephalum Species 0.000 description 1
- OYLXAWIVDOGATR-UHFFFAOYSA-N C(C)OC(C)OCC.[Cl] Chemical compound C(C)OC(C)OCC.[Cl] OYLXAWIVDOGATR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- WXPLRSVMGRAIGW-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=CS1 WXPLRSVMGRAIGW-UHFFFAOYSA-N 0.000 description 1
- DBGZLDQCMBDZIV-UHFFFAOYSA-N n-[3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-thiazol-2-ylidene]acetamide;hydrobromide Chemical compound Br.CC(=O)N=C1SC=CN1CC(=O)C1=CC=C([N+]([O-])=O)C=C1 DBGZLDQCMBDZIV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- SNJUFYRRUHWTHK-UHFFFAOYSA-N oxalic acid;6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound OC(=O)C(O)=O.N1=C2SC=CN2CC1C1=CC=CC=C1 SNJUFYRRUHWTHK-UHFFFAOYSA-N 0.000 description 1
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36663864A | 1964-05-11 | 1964-05-11 | |
| US38723164A | 1964-08-03 | 1964-08-03 | |
| US40125164A | 1964-10-02 | 1964-10-02 | |
| US446408A US3274209A (en) | 1964-05-11 | 1965-04-07 | Certain 6-substituted-imidazo[2, 1-b] thiazole compounds |
| US553595A US3364112A (en) | 1964-05-11 | 1966-03-21 | Compositions and methods employing certain 6-substituted-imidazo(2, 1-b) thiazoles as anthelmintics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117369B true NO117369B (ja) | 1969-08-04 |
Family
ID=27541299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO65158028A NO117369B (ja) | 1964-05-11 | 1965-05-10 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US3274209A (ja) |
| BE (1) | BE663591A (ja) |
| BR (1) | BR6569567D0 (ja) |
| CH (2) | CH463513A (ja) |
| CS (3) | CS158182B2 (ja) |
| DE (1) | DE1545995C3 (ja) |
| DK (3) | DK122888B (ja) |
| ES (1) | ES312813A1 (ja) |
| FI (1) | FI47193C (ja) |
| FR (1) | FR4705M (ja) |
| GB (1) | GB1043489A (ja) |
| IL (1) | IL23501A (ja) |
| IT (1) | IT1053975B (ja) |
| MY (1) | MY6900207A (ja) |
| NL (2) | NL6505806A (ja) |
| NO (1) | NO117369B (ja) |
| SE (2) | SE353095B (ja) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059588A (en) * | 1965-07-19 | 1977-11-22 | Ici Australia Limited | Process for preparing 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole |
| NL129632C (ja) * | 1965-12-10 | |||
| US3673206A (en) * | 1969-04-02 | 1972-06-27 | American Cyanamid Co | RACEMIZATION OF d({30 ) 6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZO {8 2,1-b{9 Thiazole |
| ZA704419B (en) * | 1969-07-21 | 1971-04-28 | Ici Australia Ltd | Injectable aqueous solutions of tetramisole |
| GB1287674A (en) * | 1969-07-21 | 1972-09-06 | Ici Australia Ltd | Injectable compositions |
| BR6915163D0 (pt) * | 1969-12-15 | 1973-05-31 | Cyanamid Co American | Processo quimico |
| US3673205A (en) * | 1970-03-25 | 1972-06-27 | American Cyanamid Co | 6-(m-AMINO AND SUBSTITUTED-AMINO PHENYL)-2,3,5,6-TETRAHYDRO{8 2,1-b{9 THIAZOLES AND METHOD OF USE |
| US3878222A (en) * | 1972-03-13 | 1975-04-15 | American Cyanamid Co | Methods of preparing substituted imidazothiazolium compounds |
| US3852458A (en) * | 1972-08-11 | 1974-12-03 | Janssen Pharmaceutica Nv | Antidepressive activity of tetramisole |
| DE2340633C2 (de) * | 1972-08-17 | 1985-09-05 | Janssen Pharmaceutica, N.V., Beerse | Pharmazeutische Verwendung von 2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazol |
| DE2340632C2 (de) * | 1972-08-17 | 1985-09-05 | Janssen Pharmaceutica, N.V., Beerse | Verwendung von 2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazol oder von dessen Salzen bei der unterstützenden Behandlung zur Rückbildung und Linderung von Neoplasmen |
| IE38848B1 (en) * | 1973-02-23 | 1978-06-07 | Fisons Ltd | Anthelmintic method and composition |
| US3860718A (en) * | 1973-09-20 | 1975-01-14 | Pfizer | IMIDAZO (2,1-b) THIAZOLE AND THIAZOLO (3,2-a) BENZIMIDAZOLE QUATERNARY SALTS HYPOGLYCEMIC AGENTS |
| US4042583A (en) * | 1973-09-20 | 1977-08-16 | Pfizer Inc. | Imidazo[2,1-b]thiazole and thiazolo[3,2-a]-benzimidazole quaternary salts as hypoglycemic agents and growth promotants |
| GB1541321A (en) * | 1976-03-10 | 1979-02-28 | Metabio | 2,3-dihydroimidazo(2,1-b)thiazole derivatives and process for their preparation |
| GB1516938A (en) * | 1976-05-01 | 1978-07-05 | Pfizer Ltd | Halopyridylamides of m-aminotetramisole and their use as anthelmintics |
| US4263311A (en) * | 1976-09-27 | 1981-04-21 | Smithkline Corporation | 5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles |
| GB1533347A (en) * | 1976-10-22 | 1978-11-22 | Pfizer Ltd | Anthelmintic compounds |
| US4150141A (en) * | 1977-06-28 | 1979-04-17 | Johnson & Johnson | Treatment for scabies |
| LU77703A1 (de) * | 1977-07-07 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
| US4104400A (en) * | 1977-07-08 | 1978-08-01 | E. R. Squibb & Sons, Inc. | Imidazo(2,1-b)thiazole derivatives, compositions containing same, and method of treating helminthiasis |
| US4153706A (en) * | 1978-02-13 | 1979-05-08 | Smithkline Corporation | 6-Hydroxy-5,6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazoles |
| US4153678A (en) * | 1978-07-17 | 1979-05-08 | American Cyanamid Company | Levamisole effervescent tablets |
| CA1131226A (en) * | 1978-09-28 | 1982-09-07 | Tomohiko Munakata | Heterocyclic compounds |
| PL221188A1 (ja) * | 1979-01-05 | 1980-12-01 | Ciba Geigy Ag | |
| DE3162522D1 (en) * | 1980-09-04 | 1984-04-12 | Janssen Pharmaceutica Nv | A new method of preparing 3-(2-hydroxy-2-arylethyl)-2-iminothiazolidines |
| CA1194791A (en) * | 1981-05-08 | 1985-10-08 | John M. Ballany | Parasiticidal pour-on compositions |
| US4376769A (en) * | 1981-06-19 | 1983-03-15 | Schering Corporation | Substituted imidazo thiazoles thiazines, thiazepines and thiazocines |
| AU1611383A (en) * | 1982-07-02 | 1984-01-05 | Robert Young & Company Limited | Pesticidal formulation with cypermethrin |
| ZW24186A1 (en) * | 1985-12-12 | 1987-07-08 | Smithkline Beckman Corp | Inhibition of the 5-lipoxygenase pathway |
| US5527915A (en) * | 1989-11-24 | 1996-06-18 | Janssen Pharmaceutica N.V. | Immunostimulating 6-aryl-5,6-dihydroimidazo[2,1-beta]thiazole derivatives |
| US5212192A (en) * | 1989-11-24 | 1993-05-18 | Janssen Pharmaceutica N.V. | Immunostimulating 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives |
| US5516647A (en) * | 1993-11-05 | 1996-05-14 | Abbott Laboratories | Compounds useful as alkaline phosphatase inhibitors and therapeutic agents |
| JP2001302635A (ja) * | 2000-04-21 | 2001-10-31 | Suntory Ltd | 新規複素環化合物 |
| US8067382B2 (en) * | 2002-01-08 | 2011-11-29 | Merial Limited | Anthelmintic composition |
| GB201909771D0 (en) * | 2019-07-08 | 2019-08-21 | Governing Council Of The Univ Of Toronto | Imidazothiazole compounds and methods for treating plant nematode infections |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2775538A (en) * | 1951-06-04 | 1956-12-25 | Boskamp Arthur | Stabilized hexylresorcinol therapeutic agent containing castor oil |
| US2799617A (en) * | 1953-10-21 | 1957-07-16 | British Drug Houses Ltd | Piperazine adipate compositions and treatment of helminth infections therewith |
| US2969369A (en) * | 1959-10-23 | 1961-01-24 | Searle & Co | Derivatives of 3-phenyl-5, 6-dihydroimidazo-[2. 1-b] thiazoles |
| US3147273A (en) * | 1963-05-02 | 1964-09-01 | Upjohn Co | Certain 2h-isothiazolo [4, 5-b] indol-3 (4h)-one 1-oxide compounds and their preparation |
-
0
- NL NL131034D patent/NL131034C/xx active
-
1965
- 1965-04-07 US US446408A patent/US3274209A/en not_active Expired - Lifetime
- 1965-04-29 CH CH435267A patent/CH463513A/fr unknown
- 1965-04-29 CH CH604765A patent/CH440285A/fr unknown
- 1965-05-03 GB GB18479/65A patent/GB1043489A/en not_active Expired
- 1965-05-03 DE DE1545995A patent/DE1545995C3/de not_active Expired
- 1965-05-07 NL NL6505806A patent/NL6505806A/xx unknown
- 1965-05-07 BE BE663591D patent/BE663591A/xx unknown
- 1965-05-10 IT IT10267/65A patent/IT1053975B/it active
- 1965-05-10 NO NO65158028A patent/NO117369B/no unknown
- 1965-05-10 SE SE16780/69A patent/SE353095B/xx unknown
- 1965-05-10 CS CS399772*1A patent/CS158182B2/cs unknown
- 1965-05-10 CS CS304965A patent/CS158180B2/cs unknown
- 1965-05-10 CS CS284970*1A patent/CS158181B2/cs unknown
- 1965-05-10 IL IL23501A patent/IL23501A/xx unknown
- 1965-05-10 SE SE6092/65A patent/SE321237B/xx unknown
- 1965-05-10 FI FI651133A patent/FI47193C/fi active
- 1965-05-11 BR BR169567/65A patent/BR6569567D0/pt unknown
- 1965-05-11 ES ES0312813A patent/ES312813A1/es not_active Expired
- 1965-05-11 DK DK237665AA patent/DK122888B/da unknown
- 1965-08-04 FR FR27243A patent/FR4705M/fr not_active Expired
-
1966
- 1966-03-21 US US553595A patent/US3364112A/en not_active Expired - Lifetime
- 1966-12-09 DK DK638266AA patent/DK113148B/da unknown
- 1966-12-09 DK DK638166AA patent/DK112589B/da unknown
-
1969
- 1969-12-31 MY MY1969207A patent/MY6900207A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3364112A (en) | 1968-01-16 |
| IL23501A (en) | 1968-11-27 |
| FI47193B (ja) | 1973-07-02 |
| GB1043489A (en) | 1966-09-21 |
| FI47193C (fi) | 1973-10-10 |
| CH463513A (fr) | 1968-10-15 |
| CH440285A (fr) | 1967-07-31 |
| BE663591A (ja) | 1965-11-08 |
| IT1053975B (it) | 1981-10-10 |
| CS158180B2 (ja) | 1974-10-15 |
| DE1545995C3 (de) | 1973-11-22 |
| DE1545995B2 (de) | 1973-04-26 |
| US3274209A (en) | 1966-09-20 |
| DK122888B (da) | 1972-04-24 |
| SE321237B (ja) | 1970-03-02 |
| CS158181B2 (ja) | 1974-10-15 |
| ES312813A1 (es) | 1966-02-16 |
| DK113148B (da) | 1969-02-24 |
| DE1545995A1 (de) | 1969-11-13 |
| NL131034C (ja) | |
| CS158182B2 (ja) | 1974-10-15 |
| MY6900207A (en) | 1969-12-31 |
| NL6505806A (ja) | 1965-11-12 |
| DK112589B (da) | 1968-12-30 |
| FR4705M (ja) | 1966-12-26 |
| SE353095B (ja) | 1973-01-22 |
| BR6569567D0 (pt) | 1973-08-02 |
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