HU186770B - Process for producing new benzazol derivatives - Google Patents
Process for producing new benzazol derivatives Download PDFInfo
- Publication number
- HU186770B HU186770B HU811487A HU148781A HU186770B HU 186770 B HU186770 B HU 186770B HU 811487 A HU811487 A HU 811487A HU 148781 A HU148781 A HU 148781A HU 186770 B HU186770 B HU 186770B
- Authority
- HU
- Hungary
- Prior art keywords
- salts
- tert
- butyl
- group
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 3
- -1 piperazino group Chemical group 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000007858 starting material Substances 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000000829 suppository Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- UYCMHAWOAFERFQ-UHFFFAOYSA-N 3-[(2-tert-butyl-1,3-benzothiazol-6-yl)carbamothioylsulfanyl]propanoic acid Chemical compound C1=C(NC(=S)SCCC(O)=O)C=C2SC(C(C)(C)C)=NC2=C1 UYCMHAWOAFERFQ-UHFFFAOYSA-N 0.000 claims description 3
- JRFAFNDRWHTYEF-UHFFFAOYSA-N 3-[(2-tert-butyl-5-chloro-1,3-benzothiazol-6-yl)carbamothioylsulfanyl]propanoic acid Chemical compound ClC1=C(NC(=S)SCCC(O)=O)C=C2SC(C(C)(C)C)=NC2=C1 JRFAFNDRWHTYEF-UHFFFAOYSA-N 0.000 claims description 3
- BERAVGGPNMXLJD-UHFFFAOYSA-N 3-[(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)carbamothioylsulfanyl]-2-methylpropanoic acid Chemical compound C1=C(NC(=S)SCC(C)C(O)=O)C(OC)=CC2=C1SC(C(C)(C)C)=N2 BERAVGGPNMXLJD-UHFFFAOYSA-N 0.000 claims description 3
- SGSGNVTYYAWSKN-UHFFFAOYSA-N 3-[(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)carbamothioylsulfanyl]propanoic acid Chemical compound C1=C(NC(=S)SCCC(O)=O)C(OC)=CC2=C1SC(C(C)(C)C)=N2 SGSGNVTYYAWSKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- XLCOPZULPLCNSY-UHFFFAOYSA-N n-(2-tert-butyl-1,3-benzothiazol-6-yl)-4-methylpiperazine-1-carbothioamide Chemical compound C1CN(C)CCN1C(=S)NC1=CC=C(N=C(S2)C(C)(C)C)C2=C1 XLCOPZULPLCNSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- SJXMTBVNAZUJKL-UHFFFAOYSA-N n-(2-tert-butyl-5-chloro-1,3-benzothiazol-6-yl)-4-methyl-4-oxidopiperazin-4-ium-1-carbothioamide Chemical compound C1=C2SC(C(C)(C)C)=NC2=CC(Cl)=C1NC(=S)N1CC[N+](C)([O-])CC1 SJXMTBVNAZUJKL-UHFFFAOYSA-N 0.000 claims description 2
- QGYSUGLDSVOORJ-UHFFFAOYSA-N n-(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)-4-methyl-4-oxidopiperazin-4-ium-1-carbothioamide Chemical compound COC1=CC=2N=C(C(C)(C)C)SC=2C=C1NC(=S)N1CC[N+](C)([O-])CC1 QGYSUGLDSVOORJ-UHFFFAOYSA-N 0.000 claims description 2
- QQKZAUPDCVHWJD-UHFFFAOYSA-N n-(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)-4-methylpiperazine-1-carbothioamide Chemical compound COC1=CC=2N=C(C(C)(C)C)SC=2C=C1NC(=S)N1CCN(C)CC1 QQKZAUPDCVHWJD-UHFFFAOYSA-N 0.000 claims description 2
- HOHHPQDSRCNDPW-UHFFFAOYSA-N n-(2-tert-butyl-5-methyl-1,3-benzothiazol-6-yl)-4-methylpiperazine-1-carbothioamide Chemical compound C1CN(C)CCN1C(=S)NC(C(=C1)C)=CC2=C1N=C(C(C)(C)C)S2 HOHHPQDSRCNDPW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- YLCUBKRPGJECGN-UHFFFAOYSA-N (2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)carbamothioic S-acid Chemical compound C1=C(NC(S)=O)C(OC)=CC2=C1SC(C(C)(C)C)=N2 YLCUBKRPGJECGN-UHFFFAOYSA-N 0.000 claims 1
- NEOHQLSSLPNIFZ-UHFFFAOYSA-N (2-tert-butyl-5-methyl-1,3-benzothiazol-6-yl)carbamodithioic acid Chemical compound C1=C(NC(S)=S)C(C)=CC2=C1SC(C(C)(C)C)=N2 NEOHQLSSLPNIFZ-UHFFFAOYSA-N 0.000 claims 1
- SHPVXPVEPNYFDJ-UHFFFAOYSA-N N-(2-tert-butyl-1,3-benzothiazol-6-yl)-4-(2-hydroxyethyl)piperazine-1-carbothioamide Chemical compound C1=C2SC(C(C)(C)C)=NC2=CC=C1NC(=S)N1CCN(CCO)CC1 SHPVXPVEPNYFDJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
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- 239000003208 petroleum Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
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- 238000009472 formulation Methods 0.000 description 5
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- 125000004149 thio group Chemical group *S* 0.000 description 5
- GYAHPKTUKBGNBW-UHFFFAOYSA-N 2-tert-butyl-6-isothiocyanato-1,3-benzothiazole Chemical compound C1=C(N=C=S)C=C2SC(C(C)(C)C)=NC2=C1 GYAHPKTUKBGNBW-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- MPFIWZYGVRJTAS-UHFFFAOYSA-N 3-[(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)carbamothioyloxy]propanoic acid Chemical compound C1=C(NC(=S)OCCC(O)=O)C(OC)=CC2=C1SC(C(C)(C)C)=N2 MPFIWZYGVRJTAS-UHFFFAOYSA-N 0.000 description 3
- RCTMOWLVYUEUMS-UHFFFAOYSA-N 3-[(2-tert-butyl-5-methoxy-1,3-benzothiazol-6-yl)carbamoylsulfanyl]propanoic acid Chemical compound C1=C(NC(=O)SCCC(O)=O)C(OC)=CC2=C1SC(C(C)(C)C)=N2 RCTMOWLVYUEUMS-UHFFFAOYSA-N 0.000 description 3
- ZDZBSGOEGJANKI-UHFFFAOYSA-N 3-[(2-tert-butyl-5-methyl-1,3-benzoxazol-6-yl)carbamothioylsulfanyl]propanoic acid Chemical compound C1=C(NC(=S)SCCC(O)=O)C(C)=CC2=C1OC(C(C)(C)C)=N2 ZDZBSGOEGJANKI-UHFFFAOYSA-N 0.000 description 3
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
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- 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 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
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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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH401680 | 1980-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186770B true HU186770B (en) | 1985-09-30 |
Family
ID=4268232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU811487A HU186770B (en) | 1980-05-22 | 1981-05-21 | Process for producing new benzazol derivatives |
Country Status (28)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8423697D0 (en) * | 1984-09-19 | 1984-10-24 | Ciba Geigy Ag | Benzazole derivatives |
| US5246927A (en) * | 1988-08-17 | 1993-09-21 | Ciba-Geigy Corporation | Benzazole derivatives, processes for their preparation containing such compounds and the use thereof |
| JP3095413B2 (ja) * | 1990-12-28 | 2000-10-03 | 帝人株式会社 | ベンゾオキサ縮合環化合物 |
| AU2962397A (en) * | 1996-06-07 | 1998-01-07 | Novartis Ag | Benzazole derivatives |
| US6177572B1 (en) * | 1997-08-20 | 2001-01-23 | Sepracor, Inc. | Solid and liquid-phase synthesis of benzoxazoles and benzothiazoles and their use |
| EP3235815A1 (de) * | 2016-04-19 | 2017-10-25 | Philipps-Universität Marburg | Wirkstoffe gegen parasitäre helminthen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1087561A (en) * | 1963-02-16 | 1967-10-18 | Fisons Pest Control Ltd | Fluorinated benzimidazoles and compositions containing them |
| IE31812B1 (en) * | 1967-02-03 | 1973-01-10 | Merck & Co Inc | Benzimidazole derivatives |
| US3646049A (en) * | 1970-03-05 | 1972-02-29 | Merck & Co Inc | Acylaminobenzimidazole derivatives |
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
| BE792402A (fr) * | 1971-12-07 | 1973-06-07 | Ciba Geigy | Composes heterocycliques azotes et medicaments anthelminthiqueset antimicrobiens qui en contiennent |
-
1981
- 1981-05-11 MA MA19351A patent/MA19290A1/fr unknown
- 1981-05-12 IN IN500/CAL/81A patent/IN153293B/en unknown
- 1981-05-18 FI FI811531A patent/FI75564C/fi not_active IP Right Cessation
- 1981-05-18 EP EP81810187A patent/EP0041046B1/de not_active Expired
- 1981-05-18 GB GB8115153A patent/GB2076399B/en not_active Expired
- 1981-05-18 CY CY1339A patent/CY1339A/en unknown
- 1981-05-18 DE DE8181810187T patent/DE3176402D1/de not_active Expired
- 1981-05-20 ES ES502355A patent/ES8300724A1/es not_active Expired
- 1981-05-20 MW MW21/81A patent/MW2181A1/xx unknown
- 1981-05-20 ZM ZM44/81A patent/ZM4481A1/xx unknown
- 1981-05-20 GR GR65012A patent/GR75253B/el unknown
- 1981-05-20 ZW ZW119/81A patent/ZW11981A1/xx unknown
- 1981-05-21 PT PT73066A patent/PT73066B/pt not_active IP Right Cessation
- 1981-05-21 DD DD81230154A patent/DD159073A5/de not_active IP Right Cessation
- 1981-05-21 AU AU70910/81A patent/AU547922B2/en not_active Ceased
- 1981-05-21 PH PH25662A patent/PH16754A/en unknown
- 1981-05-21 DK DK224381A patent/DK164786C/da not_active Application Discontinuation
- 1981-05-21 HU HU811487A patent/HU186770B/hu not_active IP Right Cessation
- 1981-05-21 ZA ZA19813409D patent/ZA8103409D/xx unknown
- 1981-05-21 KR KR1019810001768A patent/KR850000555B1/ko not_active Expired
- 1981-05-21 IE IE1127/81A patent/IE52426B1/en not_active IP Right Cessation
- 1981-05-21 IL IL62928A patent/IL62928A/xx not_active IP Right Cessation
- 1981-05-22 OA OA57409A patent/OA06816A/xx unknown
- 1981-05-22 JP JP7682081A patent/JPS5718670A/ja active Granted
-
1982
- 1982-06-16 ES ES513170A patent/ES8308316A1/es not_active Expired
- 1982-06-16 ES ES513169A patent/ES513169A0/es active Granted
- 1982-09-16 US US06/418,955 patent/US4511567A/en not_active Expired - Fee Related
-
1986
- 1986-06-09 KE KE3645A patent/KE3645A/xx unknown
- 1986-10-02 HK HK746/86A patent/HK74686A/xx unknown
-
1987
- 1987-12-30 MY MY141/87A patent/MY8700141A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |