DD282686A5 - Verfahren zur herstellung eines benzothiazolderivates - Google Patents

Verfahren zur herstellung eines benzothiazolderivates Download PDF

Info

Publication number: DD282686A5
Authority: DD; German Democratic Republic
Prior art keywords: group; formula; represented; lower alkyl; hydrogen atom
Prior art date: 1987-06-17

Application number

DD88316839A

Other languages

German (de)

English (en)

Inventor

Shinya Abe

Mitsuaki Miyamoto

Masayuki Tanaka

Kozo Akasaka

Kenji Hayashi

Tetsuya Kawahara

Satoshi

Yoshinori Sakuma

Takeshi Suzuki

Isao Yamatsu

Original Assignee

��@�K@�Kk��

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

1988-06-16

Publication date

1990-09-19

1988-06-16 Application filed by ��@�K@�Kk�� filed Critical ��@�K@�Kk��

1990-09-19 Publication of DD282686A5 publication Critical patent/DD282686A5/de

Links

IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 110
238000000034 method Methods 0.000 claims abstract description 56
238000006243 chemical reaction Methods 0.000 claims abstract description 37
238000002360 preparation method Methods 0.000 claims abstract description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
150000001408 amides Chemical class 0.000 claims abstract description 5
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims abstract description 4
229940116357 potassium thiocyanate Drugs 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 53
-1 bromo compound Chemical class 0.000 claims description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000003277 amino group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
150000001266 acyl halides Chemical class 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
230000017858 demethylation Effects 0.000 claims description 6
238000010520 demethylation reaction Methods 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
239000012280 lithium aluminium hydride Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
239000012954 diazonium Substances 0.000 claims description 3
150000001989 diazonium salts Chemical class 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
150000004057 1,4-benzoquinones Chemical class 0.000 claims 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
238000006193 diazotization reaction Methods 0.000 claims 1
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 claims 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
150000002617 leukotrienes Chemical class 0.000 abstract description 16
208000006673 asthma Diseases 0.000 abstract description 15
239000003814 drug Substances 0.000 abstract description 9
230000002401 inhibitory effect Effects 0.000 abstract description 6
208000026935 allergic disease Diseases 0.000 abstract description 5
229940124597 therapeutic agent Drugs 0.000 abstract description 4
206010020751 Hypersensitivity Diseases 0.000 abstract description 3
206010039085 Rhinitis allergic Diseases 0.000 abstract description 3
201000010105 allergic rhinitis Diseases 0.000 abstract description 3
230000007815 allergy Effects 0.000 abstract description 3
208000017520 skin disease Diseases 0.000 abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
208000024172 Cardiovascular disease Diseases 0.000 abstract 1
230000004048 modification Effects 0.000 abstract 1
238000012986 modification Methods 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000002904 solvent Substances 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
238000005160 1H NMR spectroscopy Methods 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000013078 crystal Substances 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 11
239000000460 chlorine Substances 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000002585 base Substances 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
238000000605 extraction Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
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 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000000924 antiasthmatic agent Substances 0.000 description 5
239000010949 copper Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 4
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 4
150000004753 Schiff bases Chemical class 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
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 4
230000003449 preventive effect Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 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
238000007112 amidation reaction Methods 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000013043 chemical agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000013076 target substance Substances 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
ZHVOWCPERPUZCF-UHFFFAOYSA-N 2-amino-4,5,7-trimethyl-1,3-benzothiazol-6-ol Chemical compound CC1=C(O)C(C)=C(C)C2=C1SC(N)=N2 ZHVOWCPERPUZCF-UHFFFAOYSA-N 0.000 description 2
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 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
206010070834 Sensitisation Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
230000009435 amidation Effects 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
208000010668 atopic eczema Diseases 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
239000002775 capsule Substances 0.000 description 2
UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 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
238000000576 coating method Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
229960000265 cromoglicic acid Drugs 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
VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000857 drug effect Effects 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 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
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
229940092253 ovalbumin Drugs 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
238000007363 ring formation reaction Methods 0.000 description 2
230000008313 sensitization Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
QIXDHVDGPXBRRD-UHFFFAOYSA-N trimethyl-p-benzoquinone Natural products CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
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
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
229940005561 1,4-benzoquinone Drugs 0.000 description 1
DHCXDJXURVPGMP-UHFFFAOYSA-N 1-(6-hydroxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)pyrrolidin-2-one Chemical compound S1C=2C(C)=C(O)C(C)=C(C)C=2N=C1N1CCCC1=O DHCXDJXURVPGMP-UHFFFAOYSA-N 0.000 description 1
YSLJVEAQUYRGBM-UHFFFAOYSA-N 1-(6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)pyrrolidin-2-one Chemical compound S1C2=C(C)C(OC)=C(C)C(C)=C2N=C1N1CCCC1=O YSLJVEAQUYRGBM-UHFFFAOYSA-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
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
RTWBJTYVSNKGGC-UHFFFAOYSA-N 2-(benzylamino)-4,5,7-trimethyl-1,3-benzothiazol-6-ol Chemical compound S1C=2C(C)=C(O)C(C)=C(C)C=2N=C1NCC1=CC=CC=C1 RTWBJTYVSNKGGC-UHFFFAOYSA-N 0.000 description 1
IIRDMUCYVJKPGB-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]-5,7-di(propan-2-yl)-1,3-benzothiazol-6-ol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC2=C1SC(N(CCO)CCO)=N2 IIRDMUCYVJKPGB-UHFFFAOYSA-N 0.000 description 1
ZNGJESOUVXCDHT-UHFFFAOYSA-N 2-amino-4,5,7-trimethyl-1,3-benzothiazol-6-ol;hydrochloride Chemical compound Cl.CC1=C(O)C(C)=C(C)C2=C1SC(N)=N2 ZNGJESOUVXCDHT-UHFFFAOYSA-N 0.000 description 1
LJDIOCJJKQCKEA-UHFFFAOYSA-N 2-amino-4-(dimethylamino)-5,7-di(propan-2-yl)-1,3-benzothiazol-6-ol Chemical compound CC(C)C1=C(O)C(C(C)C)=C2SC(N)=NC2=C1N(C)C LJDIOCJJKQCKEA-UHFFFAOYSA-N 0.000 description 1
PMFPUQYMOREONF-UHFFFAOYSA-N 2-amino-4-chlorobenzo[e][1,3]benzothiazol-5-ol Chemical compound ClC1=C(O)C2=CC=CC=C2C2=C1SC(N)=N2 PMFPUQYMOREONF-UHFFFAOYSA-N 0.000 description 1
XRWMHTFOPYEGAG-UHFFFAOYSA-N 2-aminobenzo[e][1,3]benzothiazol-5-ol Chemical compound C1=CC=C2C(N=C(S3)N)=C3C=C(O)C2=C1 XRWMHTFOPYEGAG-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
DFAMZEGRWUUOBV-UHFFFAOYSA-N 2-methoxy-3,5-di(propan-2-yl)aniline Chemical compound COC1=C(N)C=C(C(C)C)C=C1C(C)C DFAMZEGRWUUOBV-UHFFFAOYSA-N 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
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
GUAAQMHFGPSZEI-UHFFFAOYSA-N 4-[(6-hydroxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]benzoic acid Chemical compound S1C=2C(C)=C(O)C(C)=C(C)C=2N=C1NC1=CC=C(C(O)=O)C=C1 GUAAQMHFGPSZEI-UHFFFAOYSA-N 0.000 description 1
AIRYDHVYJPMRTH-UHFFFAOYSA-N 4-[[(5,7-dibromo-4-hydroxy-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NC2=C(O)C(Br)=CC(Br)=C2S1 AIRYDHVYJPMRTH-UHFFFAOYSA-N 0.000 description 1
CZTHTGORNFWZRT-UHFFFAOYSA-N 4-[[(5,7-dibromo-6-hydroxy-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NC2=CC(Br)=C(O)C(Br)=C2S1 CZTHTGORNFWZRT-UHFFFAOYSA-N 0.000 description 1
IKIAJUVGDUYASS-UHFFFAOYSA-N 4-[[(6-hydroxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound S1C=2C(C)=C(O)C(C)=C(C)C=2N=C1NCC1=CC=C(S(N)(=O)=O)C=C1 IKIAJUVGDUYASS-UHFFFAOYSA-N 0.000 description 1
WGEDHHUIAFKIBR-UHFFFAOYSA-N 4-[[(6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound S1C2=C(C)C(OC)=C(C)C(C)=C2N=C1NCC1=CC=C(S(N)(=O)=O)C=C1 WGEDHHUIAFKIBR-UHFFFAOYSA-N 0.000 description 1
JWFVZSWCHPEJTJ-UHFFFAOYSA-N 4-[[6-hydroxy-5,7-di(propan-2-yl)-1,3-benzothiazol-2-yl]amino]benzoic acid Chemical compound S1C=2C(C(C)C)=C(O)C(C(C)C)=CC=2N=C1NC1=CC=C(C(O)=O)C=C1 JWFVZSWCHPEJTJ-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
GQHIURVYQWJLSL-UHFFFAOYSA-N 4-methoxy-2,3,5-trimethylaniline Chemical compound COC1=C(C)C=C(N)C(C)=C1C GQHIURVYQWJLSL-UHFFFAOYSA-N 0.000 description 1
MPDNGVXFXZXSBR-UHFFFAOYSA-N 5,7-di(propan-2-yl)-2-(pyridin-2-ylmethylamino)-1,3-benzothiazol-6-ol Chemical compound S1C=2C(C(C)C)=C(O)C(C(C)C)=CC=2N=C1NCC1=CC=CC=N1 MPDNGVXFXZXSBR-UHFFFAOYSA-N 0.000 description 1
INXXCYFBMLFMKK-UHFFFAOYSA-N 6-methoxy-5,7-di(propan-2-yl)-1,3-benzothiazol-2-amine Chemical compound COC1=C(C(C)C)C=C2N=C(N)SC2=C1C(C)C INXXCYFBMLFMKK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
102100027313 Calsenilin Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
NVXLIZQNSVLKPO-UHFFFAOYSA-N Glucosereductone Chemical compound O=CC(O)C=O NVXLIZQNSVLKPO-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
101000726098 Homo sapiens Calsenilin Proteins 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
201000004029 Immune dysregulation-polyendocrinopathy-enteropathy-X-linked syndrome Diseases 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
GWNVDXQDILPJIG-SHSCPDMUSA-N Leukotriene C4 Natural products CCCCCC=C/CC=C/C=C/C=C/C(SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCC(=O)O)C(O)CCCC(=O)O GWNVDXQDILPJIG-SHSCPDMUSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000014435 Mentha Nutrition 0.000 description 1
241001072983 Mentha Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
101001041669 Oryctolagus cuniculus Corticostatin 1 Proteins 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000031481 Pathologic Constriction Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
201000009961 allergic asthma Diseases 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
229940116229 borneol Drugs 0.000 description 1
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
244000144987 brood Species 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
239000001354 calcium citrate Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
230000007012 clinical effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000012649 demethylating agent Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
FEAFRSXMFKTQOE-UHFFFAOYSA-N ethyl 4-[(6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]butanoate Chemical compound CC1=C(OC)C(C)=C2SC(NCCCC(=O)OCC)=NC2=C1C FEAFRSXMFKTQOE-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
229940014259 gelatin Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000011597 hartley guinea pig Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
DQQGIDYTHHAEES-UHFFFAOYSA-N n-(6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)methanesulfonamide Chemical compound COC1=C(C)C(C)=C2N=C(NS(C)(=O)=O)SC2=C1C DQQGIDYTHHAEES-UHFFFAOYSA-N 0.000 description 1
SNIXIMPOPOWTGM-UHFFFAOYSA-N n-[2-amino-6-methoxy-5,7-di(propan-2-yl)-3h-1,3-benzothiazol-2-yl]acetamide Chemical compound COC1=C(C(C)C)C=C2NC(N)(NC(C)=O)SC2=C1C(C)C SNIXIMPOPOWTGM-UHFFFAOYSA-N 0.000 description 1
FDQGSWXKNGLJAX-UHFFFAOYSA-N n-[4-amino-6-methoxy-5,7-di(propan-2-yl)-1,3-benzothiazol-2-yl]acetamide Chemical compound COC1=C(C(C)C)C(N)=C2N=C(NC(C)=O)SC2=C1C(C)C FDQGSWXKNGLJAX-UHFFFAOYSA-N 0.000 description 1
QPKXYJNIVQPBAI-UHFFFAOYSA-N n-[6-methoxy-5,7-di(propan-2-yl)-1,3-benzothiazol-2-yl]acetamide Chemical compound COC1=C(C(C)C)C=C2N=C(NC(C)=O)SC2=C1C(C)C QPKXYJNIVQPBAI-UHFFFAOYSA-N 0.000 description 1
RDVKIUVEJLLVFV-UHFFFAOYSA-N n-cyclohexyl-4-[(6-methoxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]butanamide Chemical compound S1C2=C(C)C(OC)=C(C)C(C)=C2N=C1NCCCC(=O)NC1CCCCC1 RDVKIUVEJLLVFV-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229920001778 nylon Polymers 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
239000012044 organic layer Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000036262 stenosis Effects 0.000 description 1
208000037804 stenosis Diseases 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup 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
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
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

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)

DD88316839A 1987-06-17 1988-06-16 Verfahren zur herstellung eines benzothiazolderivates DD282686A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD282686A5 true DD282686A5 (de)	1990-09-19

Family

ID=15508808

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88316839A DD282686A5 (de)	1987-06-17	1988-06-16	Verfahren zur herstellung eines benzothiazolderivates

Country Status (21)

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

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE68903484T2 (de) *	1988-12-15	1993-03-18	Rhone Poulenc Sante	2-imino-6-polyfluoralkoxy-benzothiazol-derivate, verfahren zu deren herstellung und arzneimittel, die sie enthalten.
IL97249A (en) *	1990-02-23	1995-01-24	Takeda Chemical Industries Ltd	Compounds of 7,6,5,4-tetrahydrothiazole] B-5,4 [pyridine and compounds of 5,6-dihydro-H4-pyrrolo] D-3,2 [thiazole, their manufacture, and pharmaceutical compositions including or
IE920921A1 (en) *	1991-04-04	1992-10-07	Eisai Co Ltd	Benzothiazole derivative
US5296486A (en) *	1991-09-24	1994-03-22	Boehringer Ingelheim Pharmaceuticals, Inc.	Leukotriene biosynthesis inhibitors
US5350760A (en) *	1993-08-04	1994-09-27	Merck Frosst Canada, Inc.	Aza-5,5-fused hetrocyclic acids as leukotriene antagonists
WO1997048694A1 (fr) *	1996-06-20	1997-12-24	Board Of Regents, The University Of Texas System	Composes et procedes d'obtention de preparations pharmacologiquement actives et leurs utilisations
ATE432078T1 (de)	1997-11-13	2009-06-15	Mowycal Lending Llc	Kleine peptide und methoden zur behandlung von asthma und entzündungen
GB9815696D0 (en) *	1998-07-20	1998-09-16	Pfizer Ltd	Heterocyclics
US6686357B1 (en)	1999-07-15	2004-02-03	Pfizer, Inc.	FKBP inhibitors
EP1150565A1 (fr) *	1999-02-08	2001-11-07	LION bioscience AG	Derives de thiazole et leurs banques combinatoires
EP1178977B1 (fr) *	1999-05-12	2005-06-01	Neurosearch A/S	Agents de modulation de canaux ioniques
TWI284639B (en)	2000-01-24	2007-08-01	Shionogi & Co	A compound having thrombopoietin receptor agonistic effect
JP2003532728A (ja) *	2000-05-05	2003-11-05	コーセラピューティックス，インコーポレイテッド	ヘテロ二環式スルホンアミドおよび血小板ａｄｐレセプターインヒビターとしてのそれらの使用
US6750238B1 (en) *	2000-05-12	2004-06-15	The University Of Toledo	Aralkyl ester soft drugs
US7049326B2 (en) *	2000-05-12	2006-05-23	The University Of Toledo	Method and compositions for temporarily incapacitating subjects
US6756047B2 (en) *	2000-05-12	2004-06-29	The University Of Toledo	Method and compositions for treating persistent pulmonary hypertension using aralkyl ester soft drugs
AU2001281817B2 (en)	2000-06-21	2005-11-24	F. Hoffmann-La Roche Ag	Benzothiazole derivatives
US6620811B2 (en)	2001-11-19	2003-09-16	Hoffmann-La Roche Inc.	Isonicotin- and nicotinamide derivatives of benzothiazoles
US6624163B2 (en) *	2001-11-29	2003-09-23	Hoffman-La Roche Inc.	Benzothiazole derivatives
US7338956B2 (en) *	2002-08-07	2008-03-04	Sanofi-Aventis Deutschland Gmbh	Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals
US7087761B2 (en)	2003-01-07	2006-08-08	Hoffmann-La Roche Inc.	Cyclization process for substituted benzothiazole derivatives
KR100710453B1 (ko) *	2003-05-13	2007-04-24	에프. 호프만-라 로슈 아게	아데노신 수용체 리간드로서의 2-이미다조-벤조싸이아졸
PT1636223E (pt) *	2003-05-19	2008-05-06	F Hoffmann-La Roche Ag	Derivados de benzotiazole como ligandos de receptores da adenosina
MXPA05012369A (es) *	2003-05-21	2006-02-02	Hoffmann La Roche	Derivados de benzotiazol y uso de los mismos en el tratamiento de enfermedades relacionadas con el receptor a2a de adenosina.
RU2348629C2 (ru) *	2003-05-30	2009-03-10	Ф.Хоффманн-Ля Рош Аг	Производные бензотиазола и их применение при лечении заболеваний, связанных с аденозиновыми a2a-рецепторами
US20050118291A1 (en) *	2003-09-10	2005-06-02	Mian-Ying Wang	Formulations and methods for treating breast cancer with Morinda citrifolia and methylsulfonymethane
KR100776961B1 (ko)	2003-08-12	2007-11-28	시오노기세이야쿠가부시키가이샤	트롬보포이에틴 수용체 아고니스트 작용을 가지는 화합물
RS50574B (sr)	2004-05-24	2010-05-07	F. Hoffmann-La Roche Ag.	(4-metoksi-7-morfolin-4-il-benzotiazol-2-il)-amid 4-hidroksi-4-metil-piperidin-1-karboksilne kiseline
BRPI0514099A (pt) *	2004-08-05	2008-05-27	Hoffmann La Roche	composições farmacêuticas, compostos, processo para a sua manufatura, método para o tratamento terapêutico e/ou profilático de enfermidades e utilização dos compostos
ES2309814T3 (es)	2004-11-05	2008-12-16	F. Hoffmann-La Roche Ag	Proceso para la obtencion de derivados del acido isonicotinico.
WO2006099972A1 (fr)	2005-03-23	2006-09-28	F. Hoffmann-La Roche Ag	Derives d'acetylenyl-pyrazolo-pyrimidine comme antagonistes mglur2
JP5048675B2 (ja)	2005-09-27	2012-10-17	エフ．ホフマン−ラロシュアーゲー	ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類
CN101410385B (zh)	2006-03-28	2011-08-24	高点制药有限责任公司	具有组胺h3受体活性的苯并噻唑类
MY157597A (en) *	2008-04-11	2016-06-30	Janssen Pharmaceutica Nv	Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene a4 hydrolase
UY32138A (es)	2008-09-25	2010-04-30	Boehringer Ingelheim Int	Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables
UY32470A (es)	2009-03-05	2010-10-29	Boehringer Ingelheim Int	Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones
EP2408769A1 (fr) *	2009-03-17	2012-01-25	Glaxo Group Limited	Dérivés de pyrimidine utilisés comme inhibiteurs de ltk
US8759537B2 (en)	2010-08-20	2014-06-24	Boehringer Ingelheim International Gmbh	3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents
US8586604B2 (en)	2010-08-20	2013-11-19	Boehringer Ingelheim International Gmbh	Inhibitors of the microsomal prostaglandin E2 synthase-1
US8466186B2 (en)	2010-12-10	2013-06-18	Boehringer Ingelheim International Gmbh	Compounds
US8486968B2 (en)	2010-12-10	2013-07-16	Boehringer Ingelheim International Gmbh	Compounds
UY33779A (es)	2010-12-10	2012-07-31	Boehringer Ingelheim Int	?2-(fenilamino)-1H-bencimidazol-5-carboxamidas novedosas?
CN102872012B (zh) *	2011-11-03	2015-03-25	成都医学院	一种抑制蛋白激酶化合物的用途
CN113959911B (zh) *	2020-07-20	2024-06-18	深圳迈瑞生物医疗电子股份有限公司	抗血小板聚集干扰的检测方法、试剂及其应用
CN113959912B (zh) *	2020-07-20	2024-06-21	深圳迈瑞生物医疗电子股份有限公司	抗血小板聚集干扰的白细胞检测方法、试剂及其应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2617198A (en) *	1945-06-13	1952-11-11	Better Packages Inc	Pull-out measuring tape dispenser
DE927507C (de) *	1953-02-24	1955-05-09	Bayer Ag	Verfahren zur Herstellung von Derivaten des 6-Oxy-2-aminobenzthiazols
GB808191A (en) *	1956-07-13	1959-01-28	Robert Ronald Davies	New dyestuff intermediates
US4006242A (en) *	1973-07-18	1977-02-01	Schering Corporation	Certain benzothiazoles used in the treatment of helminthiasis
AR204835A1 (es) *	1973-07-18	1976-03-05	Scherico Ltd	Procedimiento para preparar benzotiazol-2-carbamatos de etilo
DK148476C (da) *	1975-04-25	1985-12-16	Scherico Ltd	Analogifremgangsmaade til fremstilling af methyl-6-n-propoxybenzothiazol-2-carbamat
JPS5221054A (en) *	1975-08-11	1977-02-17	Teijin Ltd	Polyamide composition
DE2656468A1 (de) *	1976-12-14	1978-06-15	Boehringer Mannheim Gmbh	N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung
DE2963316D1 (en) *	1978-01-18	1982-09-02	Hoechst Ag	Process for the preparation of 2-amino-arylenothiazole compounds and their ring n-substituted derivatives
JPS5740492A (en) *	1980-08-22	1982-03-06	Yamanouchi Pharmaceut Co Ltd	Novel 2-phenylimidazo 2,1-b benzothiazole derivative
US4581457A (en) *	1984-09-21	1986-04-08	American Home Products Corporation	Heterocyclic sulfonamides

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/fr not_active Expired - Lifetime
- 1988-06-15 CA CA000569598A patent/CA1322369C/fr 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
PH26553A (en)	1992-08-19
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 (fr)	1992-11-11
HU205347B (en)	1992-04-28
PT87747A (pt)	1988-07-01
NO882627D0 (no)	1988-06-15
JP2793195B2 (ja)	1998-09-03
CA1322369C (fr)	1993-09-21
FI882692A0 (fi)	1988-06-07
ATE82276T1 (de)	1992-11-15
EP0295656A1 (fr)	1988-12-21
DK328888A (da)	1988-12-18
FI91859B (fi)	1994-05-13
KR890000451A (ko)	1989-03-14
GR3006207T3 (fr)	1993-06-21
NO170929C (no)	1993-01-06
DE3875809D1 (de)	1992-12-17
SU1731051A3 (ru)	1992-04-30
DE3875809T2 (de)	1993-04-15
NZ224946A (en)	1990-07-26

Legal Events

Date	Code	Title	Description
1998-07-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD282686A5 (de)	1990-09-19	Verfahren zur herstellung eines benzothiazolderivates
DE69613240T2 (de)	2002-04-25	N-aminoalkylfluorencarboxamide, neue klasse von dopaminerezeptor subtype spezifische liganden
DE69706660T2 (de)	2002-04-18	N-aminoalkyldibenzofuran-carboxamide als dopaminrezeptor-subtyp spezifische liganden
DE69722858T2 (de)	2004-05-13	Intimale verdickungsinhibitoren
DE2258561A1 (de)	1973-06-20	Basisch substituierte pyrimidon-(4)derivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
EP0014951A2 (fr)	1980-09-03	Dérivés hétérocycliques d'oxypropanolamine, procédé pour leur préparation et médicaments contenant ces composés
AT393507B (de)	1991-11-11	Neue purinylribofuranuronsaeurederivate, verfahren zu deren herstellung und sie enthaltende therapeutische praeparate
EP0165422B1 (fr)	1988-03-09	Bis-(4-aminophényl)-sulfones substituées, leur préparation et leur utilisation comme médicaments
DE2305092C2 (fr)	1987-10-01
DE69317399T2 (de)	1998-07-02	Aminocycloalkanobenzodioxole als beta-3 selektive adrenergische Wirkstoffe
DE3781174T2 (de)	1993-02-11	Verwendung von aromatischen diaminen fuer die behandlung von angina pectoris und diamine dafuer.
EP0271013B1 (fr)	1993-06-09	Phénylacétonitriles basiques substitués, leur préparation et des médicaments contenant ceux-ci
EP0802195A2 (fr)	1997-10-22	Dérivés de 2,3-benzodiazepine, procédé et intermédiaires pour leur obtention, composés pharmaceutiques les contenant et leur utilisation
DE2461802A1 (de)	1975-07-17	Pyrazinderivate
DE3627024A1 (de)	1987-04-02	In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine
DE3503074A1 (de)	1985-08-08	Hydantoinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten
EP0491243B1 (fr)	1996-05-15	Composés alkylaminoalkylamines et -éthers ainsi que des procédés et composés intermédiaires pour leur préparation et médicaments contenant ces composés
DE3879378T2 (de)	1993-06-24	Amid-verbindungen.
AT390952B (de)	1990-07-25	Verfahren zur herstellung von neuen furan- oder thiophenderivaten
DE69719071T2 (de)	2003-07-17	Phenanthridiniumderivate
DE69128845T2 (de)	1998-07-09	4-[3-(4-Oxothiazoldinyl)]butynylamine, Verfahren zu deren Herstellung und ihre Verwendung als Medikament
DE1964797A1 (de)	1970-07-16	Neue Amine und Verfahren zu ihrer Herstellung
DE69012407T2 (de)	1995-02-09	Imidazobenzodiazepine und ihre Salze, Verfahren zur Herstellung, Verwendung als Arzneimittel und diese Substanzen enthaltende Zusammensetzungen.
DE3901720A1 (de)	1990-07-26	Substituierte benzo(b)pyrane, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen
EP0006218B1 (fr)	1982-05-26	Acides aminés substitués, leur utilisation et leur préparation et médicaments les contenant