CH525895A - Verfahren zur Herstellung von Aminocarbonylalkylverbindungen - Google Patents

Verfahren zur Herstellung von Aminocarbonylalkylverbindungen

Info

Publication number: CH525895A
Authority: CH; Switzerland
Prior art keywords: sep; chloro; formula; group; lower alkyl
Prior art date: 1967-09-30

Application number

CH1425368A

Other languages

German (de)

English (en)

Inventor

Umio Suminori

Original Assignee

Fujisawa Pharmaceutical Co

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.)

1967-09-30

Filing date

1968-09-24

Publication date

1972-07-31

1968-09-24 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1968-09-24 Priority to CH1128171A priority Critical patent/CH526567A/de

1968-09-24 Priority to CH1128071A priority patent/CH526552A/de

1968-09-24 Priority to CH108871A priority patent/CH525899A/de

1968-09-24 Priority to CH1128271A priority patent/CH526568A/de

1968-09-24 Priority to CH1127971A priority patent/CH526551A/de

1972-07-31 Publication of CH525895A publication Critical patent/CH525895A/de

Links

125000005097 aminocarbonylalkyl group Chemical group 0.000 title claims description 6
230000003110 anti-inflammatory effect Effects 0.000 title abstract description 6
230000003288 anthiarrhythmic effect Effects 0.000 title abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 40
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000002947 alkylene group Chemical group 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
125000005277 alkyl imino group Chemical group 0.000 claims abstract description 4
-1 2-acetyloxyethyl Chemical group 0.000 claims description 147
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 92
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
YVAIFZYQODGYQY-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)CNC2=C1 YVAIFZYQODGYQY-UHFFFAOYSA-N 0.000 claims description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
238000002844 melting Methods 0.000 claims description 23
230000008018 melting Effects 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 19
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 18
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000013078 crystal Substances 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
238000001816 cooling Methods 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
239000003208 petroleum Substances 0.000 claims description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
239000002026 chloroform extract Substances 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 6
235000019341 magnesium sulphate Nutrition 0.000 claims description 6
HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 claims description 6
239000000284 extract Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000003921 oil Substances 0.000 claims description 4
IKFYMCLNOJJVFR-UHFFFAOYSA-N 2-[4-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperazin-1-yl]ethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 IKFYMCLNOJJVFR-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
239000012346 acetyl chloride Substances 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
239000011976 maleic acid Substances 0.000 claims description 3
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
239000012670 alkaline solution Substances 0.000 claims description 2
239000012230 colorless oil Substances 0.000 claims description 2
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 15
206010003119 arrhythmia Diseases 0.000 abstract description 7
230000006793 arrhythmia Effects 0.000 abstract description 7
229910052736 halogen Inorganic materials 0.000 abstract description 4
150000002367 halogens Chemical class 0.000 abstract description 4
125000001589 carboacyl group Chemical group 0.000 abstract description 3
206010061218 Inflammation Diseases 0.000 abstract 1
208000001871 Tachycardia Diseases 0.000 abstract 1
208000009729 Ventricular Premature Complexes Diseases 0.000 abstract 1
206010047289 Ventricular extrasystoles Diseases 0.000 abstract 1
125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
206010061592 cardiac fibrillation Diseases 0.000 abstract 1
230000002600 fibrillogenic effect Effects 0.000 abstract 1
230000004054 inflammatory process Effects 0.000 abstract 1
230000001314 paroxysmal effect Effects 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
230000006794 tachycardia Effects 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000008064 anhydrides Chemical class 0.000 description 8
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 6
239000007858 starting material Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
238000005576 amination reaction Methods 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
239000003937 drug carrier Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
RPRUIZPTDDIOHH-UHFFFAOYSA-N 5-chloro-3-(2-oxo-2-piperazin-1-ylethyl)-1,3-benzothiazol-2-one Chemical compound C12=CC(Cl)=CC=C2SC(=O)N1CC(=O)N1CCNCC1 RPRUIZPTDDIOHH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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 3
230000000694 effects Effects 0.000 description 3
239000011630 iodine Substances 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FYKPDAJKYKYJSL-UHFFFAOYSA-N 2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl chloride Chemical compound ClC1=CC=C2SC(=O)N(CC(=O)Cl)C2=C1 FYKPDAJKYKYJSL-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
XQFOKDKLZIETLH-UHFFFAOYSA-N 3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=CC=C12 XQFOKDKLZIETLH-UHFFFAOYSA-N 0.000 description 2
YQPGDBFDHRBTDI-UHFFFAOYSA-N 3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound FC(F)(F)C1=CC=C2SC(=O)N(CC(=O)N3CCN(CC3)C3=CC=CC=C3)C2=C1 YQPGDBFDHRBTDI-UHFFFAOYSA-N 0.000 description 2
PGVBODIHSFWKBT-UHFFFAOYSA-N 3-[2-oxo-2-[4-(2-oxopropyl)piperazin-1-yl]ethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound C(C)(=O)CN1CCN(CC1)C(=O)CN1C(SC2=C1C=C(C=C2)C(F)(F)F)=O PGVBODIHSFWKBT-UHFFFAOYSA-N 0.000 description 2
DUHTZUSPSUHUFY-UHFFFAOYSA-N 5-chloro-3-[2-[4-(3-hydroxypropyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound OCCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 DUHTZUSPSUHUFY-UHFFFAOYSA-N 0.000 description 2
WOXOJZUWCPEBQA-UHFFFAOYSA-N 5-chloro-3-[2-oxo-2-(2,4,5-trimethylpiperazin-1-yl)ethyl]-1,3-benzothiazol-2-one Chemical compound CC1CN(C(C)CN1C)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 WOXOJZUWCPEBQA-UHFFFAOYSA-N 0.000 description 2
MIKZUZOFCPJWHZ-UHFFFAOYSA-N 6-chloro-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC(Cl)=CC=C12 MIKZUZOFCPJWHZ-UHFFFAOYSA-N 0.000 description 2
VNBMVPTXOXLWHO-UHFFFAOYSA-N 6-ethoxy-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound CCOC1=CC=C2N(CC(=O)N3CCN(CCO)CC3)C(=O)SC2=C1 VNBMVPTXOXLWHO-UHFFFAOYSA-N 0.000 description 2
JUUYOZQZCKMCOW-UHFFFAOYSA-N 7-chloro-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C(Cl)C=CC=C12 JUUYOZQZCKMCOW-UHFFFAOYSA-N 0.000 description 2
206010003658 Atrial Fibrillation Diseases 0.000 description 2
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
FHFSGQKTQCYUEZ-UHFFFAOYSA-N CC(C1)N(CC#C)CC(C)N1C(CN(C(C=C(C=C1)Cl)=C1S1)C1=O)=O Chemical compound CC(C1)N(CC#C)CC(C)N1C(CN(C(C=C(C=C1)Cl)=C1S1)C1=O)=O FHFSGQKTQCYUEZ-UHFFFAOYSA-N 0.000 description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
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 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
206010042674 Swelling Diseases 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
PBTHJVDBCFJQGG-UHFFFAOYSA-N methyl azide Chemical class CN=[N+]=[N-] PBTHJVDBCFJQGG-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000001205 polyphosphate Substances 0.000 description 2
235000011176 polyphosphates Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 1
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
JBLARAPTGMIYKN-UHFFFAOYSA-N 1-[4-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperazin-1-yl]propan-2-yl 2-methylpropanoate Chemical compound CC(CN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12)OC(=O)C(C)C JBLARAPTGMIYKN-UHFFFAOYSA-N 0.000 description 1
IDPKQTSGDDPNKE-UHFFFAOYSA-N 1-[4-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperazin-1-yl]propan-2-yl acetate Chemical compound CC(CN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12)OC(C)=O IDPKQTSGDDPNKE-UHFFFAOYSA-N 0.000 description 1
WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
VRJDLVOMMNSAHU-UHFFFAOYSA-N 3-(2-morpholin-4-yl-2-oxoethyl)-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2SC(=O)N1CC(=O)N1CCOCC1 VRJDLVOMMNSAHU-UHFFFAOYSA-N 0.000 description 1
IJXCDYMALCJKGE-UHFFFAOYSA-N 3-(2-oxo-2-piperazin-1-ylethyl)-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2SC(=O)N1CC(=O)N1CCNCC1 IJXCDYMALCJKGE-UHFFFAOYSA-N 0.000 description 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
PYTKHNXADKCPEI-UHFFFAOYSA-N 3-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one Chemical compound C12=CC(Cl)=CC=C2SC(=O)N1CC(=O)N(CC1)CCN1CC1=CC=CC=C1 PYTKHNXADKCPEI-UHFFFAOYSA-N 0.000 description 1
ZRZPESLEOUBGEP-UHFFFAOYSA-N 3-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound OC1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(C=C12)C(F)(F)F ZRZPESLEOUBGEP-UHFFFAOYSA-N 0.000 description 1
SPSOCZZBSGFJKU-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C1CN(C)CCN1C(=O)CN1C(=O)SC2=CC=CC=C21 SPSOCZZBSGFJKU-UHFFFAOYSA-N 0.000 description 1
OUFMQQMIDGQTET-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound CN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(C=C12)C(F)(F)F OUFMQQMIDGQTET-UHFFFAOYSA-N 0.000 description 1
MXBMFMMVWCAQRZ-UHFFFAOYSA-N 3-[2-(aziridin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one Chemical compound ClC1=CC=C2SC(=O)N(CC(=O)N3CC3)C2=C1 MXBMFMMVWCAQRZ-UHFFFAOYSA-N 0.000 description 1
SUJAVRTWQKAKDN-UHFFFAOYSA-N 3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(C=C12)C(F)(F)F SUJAVRTWQKAKDN-UHFFFAOYSA-N 0.000 description 1
YFOABJMYANJIKL-UHFFFAOYSA-N 3-[2-[4-(2-hydroxypropyl)piperazin-1-yl]-2-oxoethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one Chemical compound CC(O)CN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(C=C12)C(F)(F)F YFOABJMYANJIKL-UHFFFAOYSA-N 0.000 description 1
IGIJSFNBEUBMGB-UHFFFAOYSA-N 4-(cyclohexyliminomethylideneamino)-n,n-diethylcyclohexan-1-amine Chemical compound C1CC(N(CC)CC)CCC1N=C=NC1CCCCC1 IGIJSFNBEUBMGB-UHFFFAOYSA-N 0.000 description 1
LJHFDTGQYCJNRM-UHFFFAOYSA-N 4-chloro-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=CC(Cl)=C12 LJHFDTGQYCJNRM-UHFFFAOYSA-N 0.000 description 1
YODVPSXHHYUKSG-UHFFFAOYSA-N 5-chloro-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C1CN(C)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 YODVPSXHHYUKSG-UHFFFAOYSA-N 0.000 description 1
PPXRJCNMEHTPSL-UHFFFAOYSA-N 5-chloro-3-[2-[4-(2-hydroxybutyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound CCC(O)CN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 PPXRJCNMEHTPSL-UHFFFAOYSA-N 0.000 description 1
FDJBXWMJALOAEO-UHFFFAOYSA-N 5-chloro-3-[2-[4-(2-hydroxyethyl)-2,5-dimethylpiperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound CC1CN(C(C)CN1CCO)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 FDJBXWMJALOAEO-UHFFFAOYSA-N 0.000 description 1
LWEBFLDXXIDUKO-UHFFFAOYSA-N 5-chloro-3-[2-[4-(2-hydroxypropyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C1CN(CC(O)C)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 LWEBFLDXXIDUKO-UHFFFAOYSA-N 0.000 description 1
AHLOLIDUOARHIK-UHFFFAOYSA-N 5-chloro-3-[2-oxo-2-[4-(2-oxopropyl)piperazin-1-yl]ethyl]-1,3-benzothiazol-2-one Chemical compound C(C)(=O)CN1CCN(CC1)C(=O)CN1C(SC2=C1C=C(C=C2)Cl)=O AHLOLIDUOARHIK-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
WLBWGEMLIMBELT-UHFFFAOYSA-N CC(C(N1CCN(CCO)CC1)=O)N(C(C=C(C=C1)Cl)=C1S1)C1=O Chemical compound CC(C(N1CCN(CCO)CC1)=O)N(C(C=C(C=C1)Cl)=C1S1)C1=O WLBWGEMLIMBELT-UHFFFAOYSA-N 0.000 description 1
OKDLKANEZMKQFQ-UHFFFAOYSA-N CC(CO)N(CC1)CCN1C(CN(C(C=C(C=C1)Cl)=C1S1)C1=O)=O Chemical compound CC(CO)N(CC1)CCN1C(CN(C(C=C(C=C1)Cl)=C1S1)C1=O)=O OKDLKANEZMKQFQ-UHFFFAOYSA-N 0.000 description 1
LSZIKYAUFNQQHZ-UHFFFAOYSA-N CC1CN(C(C)CN1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 Chemical compound CC1CN(C(C)CN1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 LSZIKYAUFNQQHZ-UHFFFAOYSA-N 0.000 description 1
FJIXOKDTADIWKG-UHFFFAOYSA-N CC=1C(=NNC=CC1)C(=O)CN1C(SC2=C1C=C(C=C2)Cl)=O Chemical compound CC=1C(=NNC=CC1)C(=O)CN1C(SC2=C1C=C(C=C2)Cl)=O FJIXOKDTADIWKG-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
206010063560 Excessive granulation tissue Diseases 0.000 description 1
206010015856 Extrasystoles Diseases 0.000 description 1
108010010803 Gelatin Proteins 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
229920000084 Gum arabic Polymers 0.000 description 1
108010076876 Keratins Proteins 0.000 description 1
102000011782 Keratins Human genes 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
JAYAGJDXJIDEKI-UHFFFAOYSA-N Lanatoside C Natural products CC1OC(OC2CC3C(C4C(C5(CCC(C5(C)C(O)C4)C=4COC(=O)C=4)O)CC3)(C)CC2)CC(O)C1OC(OC1C)CC(O)C1OC(OC1C)CC(OC(C)=O)C1OC1OC(CO)C(O)C(O)C1O JAYAGJDXJIDEKI-UHFFFAOYSA-N 0.000 description 1
JAYAGJDXJIDEKI-PTGWOZRBSA-N Lanatoside C Chemical compound O([C@H]1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]1C)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@H]([C@]4(CC[C@@H]([C@@]4(C)[C@H](O)C3)C=3COC(=O)C=3)O)CC2)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JAYAGJDXJIDEKI-PTGWOZRBSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FFUQGTVKAKOUQD-UHFFFAOYSA-N N-azidomethanamine Chemical class CNN=[N+]=[N-] FFUQGTVKAKOUQD-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
KIYZLEAKFCYATA-UHFFFAOYSA-N acetamide;1,3-benzothiazole Chemical compound CC(N)=O.C1=CC=C2SC=NC2=C1 KIYZLEAKFCYATA-UHFFFAOYSA-N 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
206010003668 atrial tachycardia Diseases 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
229940000635 beta-alanine Drugs 0.000 description 1
239000012503 blood component Substances 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000005998 bromoethyl group Chemical group 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003850 cellular structure Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
VAQYIUFEPZSFHY-UHFFFAOYSA-N ethyl 2-[4-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]-2,5-dimethylpiperazin-1-yl]acetate Chemical compound CC1N(CC(N(C1)CC(=O)OCC)C)C(=O)CN1C(SC2=C1C=C(C=C2)Cl)=O VAQYIUFEPZSFHY-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
210000001126 granulation tissue Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000002401 inhibitory effect Effects 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
239000008101 lactose Substances 0.000 description 1
229960002614 lanatoside c Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229940099273 magnesium trisilicate Drugs 0.000 description 1
229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
235000019793 magnesium trisilicate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000006072 paste Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000010269 sulphur dioxide Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 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 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
- C07D235/26—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1425368A 1967-09-30 1968-09-24 Verfahren zur Herstellung von Aminocarbonylalkylverbindungen CH525895A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH1128171A CH526567A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Benzothiazolon- und Benzimidazolon-Derivaten
CH1128071A CH526552A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Benzothiazolinon- und Benzimidazolinon-Derivaten
CH108871A CH525899A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Aminocarbonylalkylverbindungen
CH1128271A CH526568A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Benzothiazolon- und Benzimidazolon-Derivaten
CH1127971A CH526551A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Benzothiazolon- und Benzimidazolon-Derivaten

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP6287267		1967-09-30
JP8489467		1967-12-29
JP756368		1968-02-07

Publications (1)

Publication Number	Publication Date
CH525895A true CH525895A (de)	1972-07-31

Family

ID=27277657

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1425368A CH525895A (de)	1967-09-30	1968-09-24	Verfahren zur Herstellung von Aminocarbonylalkylverbindungen

Country Status (4)

Country	Link
CH (1)	CH525895A (da)
DK (1)	DK145575C (da)
FI (1)	FI51188C (da)
NL (1)	NL159105B (da)

1968
- 1968-09-20 DK DK452668A patent/DK145575C/da active
- 1968-09-24 CH CH1425368A patent/CH525895A/de not_active IP Right Cessation
- 1968-09-30 FI FI275768A patent/FI51188C/fi active
- 1968-09-30 NL NL6813976A patent/NL159105B/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI51188C (fi)	1976-11-10
DK145575B (da)	1982-12-13
DK145575C (da)	1983-07-04
NL6813976A (da)	1969-04-01
FI51188B (da)	1976-08-02
NL159105B (nl)	1979-01-15

Legal Events

Date	Code	Title	Description
1986-05-30	PL	Patent ceased

Publication	Publication Date	Title
DE69011059T2 (de)	1995-03-02	Heterozyklische Acylaminothiazolderivate, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen.
CH624395A5 (da)	1981-07-31
CH667268A5 (de)	1988-09-30	1,2-benzisothiazol-3-ylpiperazine.
DE1770571C3 (de)	1980-10-16	2-Oxo-3-benzothiazolinacetamid-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2557342A1 (de)	1977-06-30	Basisch substituierte indolderivate und verfahren zu ihrer herstellung
DE3444046A1 (de)	1985-12-12	N-acylierte diamidderivate saurer aminosaeuren, deren salze, verfahren zur herstellung derselben und anti-ulcus-mittel mit einem gehalt derselben
EP0116360B1 (de)	1987-07-01	1-Phenyl-2-aminocarbonylindol-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0039519B1 (de)	1984-05-02	Substituierte Thienotricyclen, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2938571C2 (da)	1988-02-18
DE2315148A1 (de)	1973-10-18	Neue chinolinderivate, verfahren zu ihrer herstellung und ihre verwendung
CH633288A5 (de)	1982-11-30	Verfahren zur herstellung von neuen heterocyclylaminoderivaten.
WO1979000426A1 (fr)	1979-07-12	Diamine cyclique n, n'-disubstituee et procede pour sa preparation
DE3424586A1 (de)	1986-01-09	3-aminocarbonylmethoxy-5-phenyl-pyrazol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US3624086A (en)	1971-11-30	Adamantanecarboxamidoalkanoic acid amides
AT287705B (de)	1971-02-10	Verfahren zur Herstellung von neuen Benzthiazolinon- oder Benzimidazolinonderivaten und ihren Salzen
DD258812A1 (de)	1988-08-03	Verfahren zur herstellung neuer ixoxazolderivate
DE2442851A1 (de)	1976-03-18	Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung
DD232045A5 (de)	1986-01-15	Verfahren zur herstellung von vorwirkstoffen entzuendungshemmender oxicame
CH525899A (de)	1972-07-31	Verfahren zur Herstellung von Aminocarbonylalkylverbindungen
DE3445011A1 (de)	1985-06-13	Neues anilinderivat, verfahren zu seiner herstellung und seine verwendung
DE1095836B (de)	1960-12-29	Verfahren zur Herstellung von in 10-Stellung basisch substituierten Phenthiazinderivaten
DE2012667A1 (de)	1970-10-01	Acyloxyalky!verbindungen, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0011092A1 (de)	1980-05-28	Alpha-Aminophenylessigsäurederivate zur Verwendung bei der Behandlung von Entzündungen sowie neue alpha-Aminophenylessigsäurederivate
AT346841B (de)	1978-11-27	Verfahren zur herstellung von neuen 3- phenylindolinen und ihren salzen
AT257624B (de)	1967-10-10	Verfahren zur Herstellung von neuen Phenthiazinderivaten und ihren Salzen