FI64587C - Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-(substituerad-bensoyl-imino)-5-nitro-4-tiazoliner - Google Patents

Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-(substituerad-bensoyl-imino)-5-nitro-4-tiazoliner Download PDF

Info

Publication number: FI64587C
Authority: FI; Finland
Prior art keywords: nitro; formula; diacetamide; iii; compound
Prior art date: 1979-12-21

Application number

FI803980A

Other languages

English (en)

Finnish (fi)

Other versions

FI803980L (fi

FI64587B (fi

Inventor

Peter John Islip

Mirjana Vladimira Bogunovic

Original Assignee

Wellcome Found

Priority date (The priority date 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 date listed.)

1979-12-21

Filing date

1980-12-19

Publication date

1983-12-12

1980-12-19 Application filed by Wellcome Found filed Critical Wellcome Found

1981-06-22 Publication of FI803980L publication Critical patent/FI803980L/fi

1983-08-31 Publication of FI64587B publication Critical patent/FI64587B/fi

1983-12-12 Application granted granted Critical

1983-12-12 Publication of FI64587C publication Critical patent/FI64587C/fi

Links

239000000203 mixture Substances 0.000 title description 26
238000009472 formulation Methods 0.000 title description 20
239000003814 drug Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 47
-1 2- (substituted-benzoylamino) -5-nitro-4-thiazolines Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000000725 suspension Substances 0.000 description 13
238000001953 recrystallisation Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
241000282693 Cercopithecidae Species 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000004615 ingredient Substances 0.000 description 9
239000002585 base Substances 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
239000006185 dispersion Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 6
229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000002285 corn oil Substances 0.000 description 6
235000005687 corn oil Nutrition 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
235000010446 mineral oil Nutrition 0.000 description 6
239000001267 polyvinylpyrrolidone Substances 0.000 description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000002775 capsule Substances 0.000 description 5
230000006378 damage Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000005336 cracking Methods 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000007918 intramuscular administration Methods 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 description 3
SXAHCKRILHYOCW-UHFFFAOYSA-N 2-methyl-n-(5-nitro-1,3-thiazol-2-yl)benzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 SXAHCKRILHYOCW-UHFFFAOYSA-N 0.000 description 3
VIQLIJJZBHGRDL-UHFFFAOYSA-N 2-nitro-n-(5-nitro-1,3-thiazol-2-yl)benzamide Chemical compound S1C([N+](=O)[O-])=CN=C1NC(=O)C1=CC=CC=C1[N+]([O-])=O VIQLIJJZBHGRDL-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002125 Sokalan® Polymers 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
230000000507 anthelmentic effect Effects 0.000 description 3
229960001631 carbomer Drugs 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
229920002678 cellulose Polymers 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
235000013601 eggs Nutrition 0.000 description 3
210000003608 fece Anatomy 0.000 description 3
230000035876 healing Effects 0.000 description 3
239000005457 ice water Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
229940100692 oral suspension Drugs 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000008213 purified water Substances 0.000 description 3
239000008109 sodium starch glycolate Substances 0.000 description 3
229920003109 sodium starch glycolate Polymers 0.000 description 3
229940079832 sodium starch glycolate Drugs 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
238000005303 weighing Methods 0.000 description 3
GEEQQCJPOJEDIN-UHFFFAOYSA-N 2-(2-imino-5-nitro-1,3-thiazol-3-yl)acetamide Chemical compound N=C1SC(=CN1CC(=O)N)[N+](=O)[O-] GEEQQCJPOJEDIN-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
QOMKVOBREOBFKL-UHFFFAOYSA-N 2-chloro-n-(5-nitro-1,3-thiazol-2-yl)benzamide Chemical compound S1C([N+](=O)[O-])=CN=C1NC(=O)C1=CC=CC=C1Cl QOMKVOBREOBFKL-UHFFFAOYSA-N 0.000 description 2
OPBKNMADLYAGCV-UHFFFAOYSA-N 2-nitro-4,5-dihydro-1,3-thiazole Chemical class [O-][N+](=O)C1=NCCS1 OPBKNMADLYAGCV-UHFFFAOYSA-N 0.000 description 2
QFPGKQYYQDTOFV-UHFFFAOYSA-N 3-nitro-n-(5-nitro-1,3-thiazol-2-yl)benzamide Chemical compound S1C([N+](=O)[O-])=CN=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 QFPGKQYYQDTOFV-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001494479 Pecora Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
241000242678 Schistosoma Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 2
238000000465 moulding Methods 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
ODYHDOOILNJSNM-UHFFFAOYSA-N C1=CC=C(C=C1)C(=O)NC2N(C=C(S2)[N+](=O)[O-])CC(=O)N Chemical compound C1=CC=C(C=C1)C(=O)NC2N(C=C(S2)[N+](=O)[O-])CC(=O)N ODYHDOOILNJSNM-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241000577979 Peromyscus spicilegus Species 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
241000242679 Schistosoma bovis Species 0.000 description 1
241000242683 Schistosoma haematobium Species 0.000 description 1
241001442512 Schistosoma mattheei Species 0.000 description 1
244000046101 Sophora japonica Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
150000003869 acetamides Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940124339 anthelmintic agent Drugs 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000009826 distribution Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012052 hydrophilic carrier Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
AIGLQRIURDEQJG-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-5-nitro-1,3-thiazol-2-ylidene]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)N=C1N(CC(N)=O)C=C([N+]([O-])=O)S1 AIGLQRIURDEQJG-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
239000011148 porous material Substances 0.000 description 1
210000003240 portal vein Anatomy 0.000 description 1
238000011084 recovery Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000007962 solid dispersion Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000009736 wetting Methods 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
- C07D277/20—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
- C07D277/58—Nitro radicals
- 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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)
Plural Heterocyclic Compounds (AREA)

FI803980A 1979-12-21 1980-12-19 Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-(substituerad-bensoyl-imino)-5-nitro-4-tiazoliner FI64587C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7944276		1979-12-21
GB7944276		1979-12-21

Publications (3)

Publication Number	Publication Date
FI803980L FI803980L (fi)	1981-06-22
FI64587B FI64587B (fi)	1983-08-31
FI64587C true FI64587C (fi)	1983-12-12

Family

ID=10510031

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI803980A FI64587C (fi)	1979-12-21	1980-12-19	Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-(substituerad-bensoyl-imino)-5-nitro-4-tiazoliner

Country Status (14)

Country	Link
US (1)	US4379156A (da)
EP (1)	EP0031563B1 (da)
JP (1)	JPS5697278A (da)
AR (1)	AR226579A1 (da)
AU (1)	AU540080B2 (da)
BR (1)	BR8008393A (da)
DE (1)	DE3064852D1 (da)
DK (1)	DK147856C (da)
FI (1)	FI64587C (da)
HU (1)	HU180396B (da)
IL (1)	IL61772A (da)
IT (1)	IT1144025B (da)
PH (1)	PH16300A (da)
ZA (1)	ZA807940B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3919365A1 (de) *	1989-06-14	1990-12-20	Bayer Ag	2-acylamino-4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung in schaedlingsbekaempfungsmitteln und neue zwischenprodukte
WO2014052831A1 (en) *	2012-09-28	2014-04-03	Xavier University Of Louisiana	Anti-migration and anti-invasion thiazole analogs for treatment of cellular proliferative disease

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA709399A (en) *		1965-05-11	L.A. Pons Andre	Thiazolic derivatives and method for preparing same
GB1158751A (en) *	1967-03-06	1969-07-16	Parke Davis & Co	New 2-Imino-5-Nitrothiazoline Compounds and methods for their production
US3523122A (en) *	1969-02-03	1970-08-04	Parke Davis & Co	Novel 5-nitro-4-thiazolin-2-ylidene compounds
GB1212326A (en) *	1969-06-18	1970-11-11	Parke Davis & Co	New 5-nitro-4-thiazoline-3-acetamide compounds and methods for their production
GB1245916A (en) *	1970-03-11	1971-09-15	Parke Davis & Co	New thiazoline compounds and methods for their production
GB1437800A (en) *	1973-08-08	1976-06-03	Phavic Sprl	Derivatives of 2-benzamido-5-nitro-thiazoles

1980
- 1980-12-19 EP EP80108066A patent/EP0031563B1/en not_active Expired
- 1980-12-19 IT IT50426/80A patent/IT1144025B/it active
- 1980-12-19 DE DE8080108066T patent/DE3064852D1/de not_active Expired
- 1980-12-19 DK DK545280A patent/DK147856C/da not_active IP Right Cessation
- 1980-12-19 AR AR283733A patent/AR226579A1/es active
- 1980-12-19 HU HU80803061A patent/HU180396B/hu unknown
- 1980-12-19 AU AU65542/80A patent/AU540080B2/en not_active Ceased
- 1980-12-19 PH PH25009A patent/PH16300A/en unknown
- 1980-12-19 FI FI803980A patent/FI64587C/fi not_active IP Right Cessation
- 1980-12-19 IL IL61772A patent/IL61772A/xx unknown
- 1980-12-19 ZA ZA00807940A patent/ZA807940B/xx unknown
- 1980-12-19 JP JP18030880A patent/JPS5697278A/ja active Pending
- 1980-12-19 BR BR8008393A patent/BR8008393A/pt unknown
- 1980-12-22 US US06/218,553 patent/US4379156A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FI803980L (fi)	1981-06-22
DE3064852D1 (en)	1983-10-20
IL61772A0 (en)	1981-01-30
DK545280A (da)	1981-06-22
US4379156A (en)	1983-04-05
IT8050426A0 (it)	1980-12-19
EP0031563A1 (en)	1981-07-08
IT1144025B (it)	1986-10-29
AU540080B2 (en)	1984-11-01
AU6554280A (en)	1981-06-25
FI64587B (fi)	1983-08-31
DK147856C (da)	1985-06-10
BR8008393A (pt)	1981-07-07
DK147856B (da)	1984-12-24
EP0031563B1 (en)	1983-09-14
AR226579A1 (es)	1982-07-30
IL61772A (en)	1984-03-30
HU180396B (en)	1983-02-28
ZA807940B (en)	1982-07-28
PH16300A (en)	1983-09-05
JPS5697278A (en)	1981-08-05

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: THE WELLCOME FOUNDATION LIMITED

Publication	Publication Date	Title
CN100542530C (zh)	2009-09-23	3′－[(2z)－[1－(3,4－二甲基苯基)－1,5－二氢－3－甲基－5－氧代－4h－吡唑－4－亚基]肼基]－2′－羟基－[ 1,1′－联苯基]－3－羧酸二－(单乙醇胺)
US4512998A (en)	1985-04-23	Anthelmintic benzimidazole carbamates
CN101445492B (zh)	2012-05-30	酰胺基噻唑衍生物、其制备方法和用途
AU3030399A (en)	1999-09-20	Nitrate salt of anti-ulcer medicine
KR880000786B1 (ko)	1988-05-09	피페라진 유도체의 제조방법
FI64587C (fi)	1983-12-12	Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-(substituerad-bensoyl-imino)-5-nitro-4-tiazoliner
EA014101B1 (ru)	2010-08-30	Антагонист cd80
KR860001578B1 (ko)	1986-10-10	3-티오메틸 파리딘 유도체의 제조방법
US4151188A (en)	1979-04-24	Arsenamide compound
DE2231067C2 (de)	1982-02-04	Phenoxathiinderivate, Verfahren zu deren Herstellung sowie pharmazeutische Präparate mit einem Gehalt an Phenoxathiinderivaten zur Bekämpfung von Virusinfektionen
CN101550112B (zh)	2011-04-06	4,5-二取代噻唑衍生物、其制备方法和用途
JPH02223560A (ja)	1990-09-05	イミダゾリン誘導体を含有する宿主動物の外部寄生虫の浸透性防除剤および新規なイミダゾリン誘導体
AU723267B2 (en)	2000-08-24	Modified form of the R(-)-N-(4,4-di(3-methylthien-2-yl) but-3-enyl)-nipecotic acid hydrochloride
CA1158558A (en)	1983-12-13	Antidiarrhoeal agents
EP0075140A1 (de)	1983-03-30	Tricyclische Thiazolyloxamidsäuren und Derivate, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel
CA1133913A (en)	1982-10-19	N-(1-methyl-2-pyrrolidinyl-methyl)-2,3- dimethoxy-5-methylsulphamoyl benzamide and its derivatives, their preparation processes and their use in the treatment of disorders of the lower urinary apparatus
US3535331A (en)	1970-10-20	Water-soluble 2-substituted benzimidazole hypophosphite salts
WO2008108842A1 (en)	2008-09-12	Lisofylline analogs and methods for use
KR102146742B1 (ko)	2020-08-21	동물의 바이러스 질환 예방 또는 치료용 조성물
US6822098B2 (en)	2004-11-23	Ester or amide derivatives
US3538108A (en)	1970-11-03	Water - soluble 2 - substituted benzimidazole methanesulfonic acid salts
US4218447A (en)	1980-08-19	Acyl derivatives of hellebrigenin
DE2755122C2 (de)	1983-06-30	Neue Acylderivate des Hellebrigenins, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
US3326753A (en)	1967-06-20	Benzimidazole anthelmintic compositions and method of use
WO2005023803A1 (en)	2005-03-17	Phosphoric acid salt of 5-[[4-[2-(methyl-2-pyridinylamino) ethoxy] phenyl] methyl]- 2,4-thiazolidinedione