PH26553A - Benzothiazole derivatives - Google Patents

Benzothiazole derivatives Download PDF

Info

Publication number: PH26553A
Authority: PH; Philippines
Prior art keywords: group; lower alkyl; compound; formula; alkyl group
Prior art date: 1987-06-17

Application number

PH37022A

Other languages

English (en)

Inventor

Shinya Abe

Masayuki Tanaka

Kenji Hayashi

Satoshi Katayama

Takeshi Zusuki

Mitsuaki Miyamoto

Kozo Akasaka

Tetsuya Kawahara

Yoshinori Sakuma

Isao Yamatsu

Original Assignee

Eisai Co Ltd

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.)

1987-06-17

Filing date

1988-08-08

Publication date

1992-08-19

1988-08-08 Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd

1992-08-19 Publication of PH26553A publication Critical patent/PH26553A/en

Links

IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 109
-1 benzothiazole compound Chemical class 0.000 claims abstract description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims description 59
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
XUKYAGRJUUZOCZ-UHFFFAOYSA-N 2,4,5-trimethyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC(C)=NC2=C1C XUKYAGRJUUZOCZ-UHFFFAOYSA-N 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 1
240000002329 Inga feuillei Species 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
150000002617 leukotrienes Chemical class 0.000 abstract description 16
208000006673 asthma Diseases 0.000 abstract description 10
238000004519 manufacturing process Methods 0.000 abstract description 8
208000026935 allergic disease Diseases 0.000 abstract description 3
150000001408 amides Chemical class 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
206010020751 Hypersensitivity Diseases 0.000 abstract description 2
230000007815 allergy Effects 0.000 abstract description 2
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
206010039085 Rhinitis allergic Diseases 0.000 abstract 1
201000010105 allergic rhinitis Diseases 0.000 abstract 1
210000000748 cardiovascular system Anatomy 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
238000000034 method Methods 0.000 description 45
239000002904 solvent Substances 0.000 description 41
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000000460 chlorine Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000000605 extraction Methods 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002585 base Substances 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
239000000924 antiasthmatic agent Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000017858 demethylation Effects 0.000 description 5
238000010520 demethylation reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
150000001266 acyl halides Chemical class 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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 3
150000004753 Schiff bases Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000003086 colorant Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000008187 granular material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000003449 preventive effect Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
AZOZOHCZAFSZIG-UHFFFAOYSA-N 2,4-dibromo-1,3-benzothiazole Chemical compound C1=CC=C2SC(Br)=NC2=C1Br AZOZOHCZAFSZIG-UHFFFAOYSA-N 0.000 description 2
OJKLTHIQRARJCE-UHFFFAOYSA-N 2-methoxy-1,3-benzothiazole Chemical compound C1=CC=C2SC(OC)=NC2=C1 OJKLTHIQRARJCE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
102000003820 Lipoxygenases Human genes 0.000 description 2
108090000128 Lipoxygenases Proteins 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
206010070834 Sensitisation Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
239000000043 antiallergic agent Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000007012 clinical effect Effects 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
229960000265 cromoglicic acid Drugs 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 2
239000000314 lubricant 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
239000000463 material Substances 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
230000008313 sensitization Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000008279 sol Substances 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
235000013616 tea Nutrition 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
210000003371 toe Anatomy 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
VPDYNEQGOXGPEN-UHFFFAOYSA-N 2,4-di(propan-2-yl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(C(C)C)=NC2=C1C(C)C VPDYNEQGOXGPEN-UHFFFAOYSA-N 0.000 description 1
SCOFVNRJAKETCM-UHFFFAOYSA-N 2-bromo-6-methoxy-5,7-di(propan-2-yl)-1,3-benzothiazole Chemical compound COC1=C(C(C)C)C=C2N=C(Br)SC2=C1C(C)C SCOFVNRJAKETCM-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
HUVORRPTACOVPT-UHFFFAOYSA-N 6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-amine Chemical compound COC1=C(C)C(C)=C2N=C(N)SC2=C1C HUVORRPTACOVPT-UHFFFAOYSA-N 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000005922 tert-pentoxy group Chemical group 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
235000013337 tricalcium citrate Nutrition 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- C07D277/68—Benzothiazoles 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
- C07D277/82—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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paper (AREA)

PH37022A 1987-06-17 1988-08-08 Benzothiazole derivatives PH26553A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15098787		1987-06-17

Publications (1)

Publication Number	Publication Date
PH26553A true PH26553A (en)	1992-08-19

Family

ID=15508808

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH37022A PH26553A (en)	1987-06-17	1988-08-08	Benzothiazole derivatives

Country Status (21)

Country	Link
US (1)	US4929623A (de)
EP (1)	EP0295656B1 (de)
JP (1)	JP2793195B2 (de)
KR (1)	KR910005709B1 (de)
CN (1)	CN1030757A (de)
AT (1)	ATE82276T1 (de)
AU (1)	AU610186B2 (de)
CA (1)	CA1322369C (de)
DD (1)	DD282686A5 (de)
DE (1)	DE3875809T2 (de)
DK (1)	DK328888A (de)
ES (1)	ES2045017T3 (de)
FI (1)	FI91859C (de)
GR (1)	GR3006207T3 (de)
HU (1)	HU205347B (de)
NO (1)	NO170929C (de)
NZ (1)	NZ224946A (de)
PH (1)	PH26553A (de)
PT (1)	PT87747B (de)
SU (1)	SU1731051A3 (de)
ZA (1)	ZA884277B (de)

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KR100776961B1 (ko)	2003-08-12	2007-11-28	시오노기세이야쿠가부시키가이샤	트롬보포이에틴 수용체 아고니스트 작용을 가지는 화합물
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1988
- 1988-06-07 FI FI882692A patent/FI91859C/fi not_active IP Right Cessation
- 1988-06-08 NZ NZ224946A patent/NZ224946A/xx unknown
- 1988-06-15 ZA ZA884277A patent/ZA884277B/xx unknown
- 1988-06-15 DE DE8888109552T patent/DE3875809T2/de not_active Expired - Fee Related
- 1988-06-15 ES ES88109552T patent/ES2045017T3/es not_active Expired - Lifetime
- 1988-06-15 JP JP63147141A patent/JP2793195B2/ja not_active Expired - Lifetime
- 1988-06-15 EP EP88109552A patent/EP0295656B1/de not_active Expired - Lifetime
- 1988-06-15 CA CA000569598A patent/CA1322369C/en not_active Expired - Fee Related
- 1988-06-15 NO NO882627A patent/NO170929C/no unknown
- 1988-06-15 AT AT88109552T patent/ATE82276T1/de active
- 1988-06-16 SU SU884356028A patent/SU1731051A3/ru active
- 1988-06-16 HU HU883098A patent/HU205347B/hu not_active IP Right Cessation
- 1988-06-16 DD DD88316839A patent/DD282686A5/de not_active IP Right Cessation
- 1988-06-16 DK DK328888A patent/DK328888A/da not_active Application Discontinuation
- 1988-06-16 AU AU17699/88A patent/AU610186B2/en not_active Ceased
- 1988-06-16 US US07/207,329 patent/US4929623A/en not_active Expired - Fee Related
- 1988-06-16 PT PT87747A patent/PT87747B/pt not_active IP Right Cessation
- 1988-06-17 CN CN88103660A patent/CN1030757A/zh active Pending
- 1988-06-17 KR KR1019880007320A patent/KR910005709B1/ko not_active Expired
- 1988-08-08 PH PH37022A patent/PH26553A/en unknown
1992
- 1992-11-12 GR GR920401328T patent/GR3006207T3/el unknown

Also Published As

Publication number	Publication date
ES2045017T3 (es)	1994-01-16
NO882627L (no)	1988-12-19
NO170929B (no)	1992-09-21
HUT47554A (en)	1989-03-28
ZA884277B (en)	1989-03-29
US4929623A (en)	1990-05-29
AU1769988A (en)	1988-12-22
CN1030757A (zh)	1989-02-01
PT87747B (pt)	1992-10-30
FI882692L (fi)	1988-12-18
FI91859C (fi)	1994-08-25
AU610186B2 (en)	1991-05-16
JPS6479162A (en)	1989-03-24
KR910005709B1 (ko)	1991-08-02
DK328888D0 (da)	1988-06-16
EP0295656B1 (de)	1992-11-11
HU205347B (en)	1992-04-28
PT87747A (pt)	1988-07-01
NO882627D0 (no)	1988-06-15
JP2793195B2 (ja)	1998-09-03
CA1322369C (en)	1993-09-21
FI882692A0 (fi)	1988-06-07
ATE82276T1 (de)	1992-11-15
EP0295656A1 (de)	1988-12-21
DK328888A (da)	1988-12-18
FI91859B (fi)	1994-05-13
KR890000451A (ko)	1989-03-14
GR3006207T3 (de)	1993-06-21
NO170929C (no)	1993-01-06
DE3875809D1 (de)	1992-12-17
SU1731051A3 (ru)	1992-04-30
DD282686A5 (de)	1990-09-19
DE3875809T2 (de)	1993-04-15
NZ224946A (en)	1990-07-26

Publication	Publication Date	Title
PH26553A (en)	1992-08-19	Benzothiazole derivatives
DE69906938T2 (de)	2004-02-26	Glococorticoid selektive entzündungshemmende mittel
DD283395A5 (de)	1990-10-10	Verfahren zur herstellung von tetrahydropyridinen
PL145420B1 (en)	1988-09-30	Method of obtaining novel substituted polycarbocyclic aromatic amine alkanoles
WO1992012981A1 (en)	1992-08-06	Substituted phenyl-1,3 dioxoloquinoline derivatives and their use as antitumor agents
NZ209494A (en)	1987-03-06	Sulphamates,intermediates and pharmaceutical compositions
US4087547A (en)	1978-05-02	Hexahydro-dibenzo[b,d]pyran-9-ones in treatment of glaucoma
US3944673A (en)	1976-03-16	Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs
FI88717B (fi)	1993-03-15	Foerfarande foer framstaellning av som laekemedel anvaendbara cyklopenta/d/pyrimidinderivat
GB2211501A (en)	1989-07-05	Antihypertensive benzopyran derivatives
IE782217L (en)	1979-05-10	4, 9-DIHYDRO-4, 9-DIOXO-1H-NAPHTHO (2, 3-d) TRIAZOLES
AU674167B2 (en)	1996-12-12	Benzopyranones, method of preparing them and their use
GB1574665A (en)	1980-09-10	3,4-dihydrocarbostyril derivatives and process for preparing the same
RU2060249C1 (ru)	1996-05-20	Полициклические биоцидные соединения и фармацевтическая композиция на их основе
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US3849405A (en)	1974-11-19	Thieno-(2,3-e)(1,4)diazepin-2-ones
JPS5576873A (en)	1980-06-10	Coumarin derivative, its preparation, and antiallergic drugs containing it as active constituent
Groutas et al.	1984	Synthesis and antitumor activity of some aromatic selenolactones
DD251289A5 (de)	1987-11-11	Verfahren zur herstellung einer neuartigen racemischen oder optisch aktiven verbindung
DD209452A5 (de)	1984-05-09	Verfahren zur herstellung von 5,6-dihydro-1 1h-dibenzo (b,e)-azepin-6-onen
PL121605B1 (en)	1982-05-31	Proces for preparing 5-substituted 10,11-dihydro-5h-dibenzo-/a,d/cyclohepteno-5,10-imineszo ciklogepten-5,10-iminov
US4330554A (en)	1982-05-18	Spirobenzofuranone compounds
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DE2208535A1 (de)	1973-08-30	Neue pyrido eckige klammer auf 3,2-d eckige klammer zu pyrimidine
DE69033324T2 (de)	2000-07-27	Verbindungen der 1,4-bis(amino)benzo(g)phthalazenreihe