CH616423A5 - - Google Patents

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Info

Publication number: CH616423A5
Authority: CH; Switzerland
Prior art keywords: group; alkyl; formula; tetrazolyl; compound
Prior art date: 1972-05-19

Application number

CH713973A

Other languages

German (de)

English (en)

Inventor

Harold Francis Hodson

John Frederick Batchelor

Original Assignee

Wellcome Found

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1972-05-19

Filing date

1973-05-18

Publication date

1980-03-31

1973-05-18 Application filed by Wellcome Found filed Critical Wellcome Found

1980-03-31 Publication of CH616423A5 publication Critical patent/CH616423A5/de

Links

238000002360 preparation method Methods 0.000 claims description 65
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 26
-1 5-tetrazolyl Chemical group 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 17
VIDCTSLIEZMQRF-UHFFFAOYSA-N 10,10-dioxo-3-(2h-tetrazol-5-yl)thioxanthen-9-one Chemical compound C=1C=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=CC=1C=1N=NNN=1 VIDCTSLIEZMQRF-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
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 description 5
230000002378 acidificating effect Effects 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
DRIRMYPZOAOUPR-UHFFFAOYSA-N 10,10-dioxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1 DRIRMYPZOAOUPR-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
239000000243 solution Substances 0.000 description 34
239000000203 mixture Substances 0.000 description 33
239000000047 product Substances 0.000 description 26
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
239000007787 solid Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 18
239000004480 active ingredient Substances 0.000 description 16
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 10
208000006673 asthma Diseases 0.000 description 9
239000000843 powder Substances 0.000 description 9
KTMTUGYSHWKLNN-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 KTMTUGYSHWKLNN-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
239000002245 particle Substances 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 7
238000009835 boiling Methods 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
230000002685 pulmonary effect Effects 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000011282 treatment Methods 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
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 5
150000002148 esters Chemical class 0.000 description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
FATBSHSMRFRICI-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 FATBSHSMRFRICI-UHFFFAOYSA-N 0.000 description 4
NECFGXHWUOZZSE-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)N)=CC=C3C(=O)C2=C1 NECFGXHWUOZZSE-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000000427 antigen Substances 0.000 description 4
102000036639 antigens Human genes 0.000 description 4
108091007433 antigens Proteins 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000006196 drop Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
210000003491 skin Anatomy 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
AVTIJIQJHHIUBL-UHFFFAOYSA-N 10,10-dioxothianthrene-2-carbonitrile Chemical compound C1=C(C#N)C=C2S(=O)(=O)C3=CC=CC=C3SC2=C1 AVTIJIQJHHIUBL-UHFFFAOYSA-N 0.000 description 3
WOTFCARJUHUAST-UHFFFAOYSA-N 2-(benzenesulfonyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(S(=O)(=O)C=2C=CC=CC=2)=C1 WOTFCARJUHUAST-UHFFFAOYSA-N 0.000 description 3
OFQWOKQMFNXHKD-UHFFFAOYSA-N 2-methyl-10,10-dioxothioxanthen-9-one Chemical compound C1=CC=C2S(=O)(=O)C3=CC=C(C)C=C3C(=O)C2=C1 OFQWOKQMFNXHKD-UHFFFAOYSA-N 0.000 description 3
KFTPXAFBDZWJNK-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carbonitrile Chemical compound N#CC1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1 KFTPXAFBDZWJNK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
239000004604 Blowing Agent Substances 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
201000009961 allergic asthma Diseases 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
229940124630 bronchodilator Drugs 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
210000000214 mouth Anatomy 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
QZKVUSSYPPWURQ-UHFFFAOYSA-N 1-methylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C QZKVUSSYPPWURQ-UHFFFAOYSA-N 0.000 description 2
NTIVMTODXGIOHE-UHFFFAOYSA-N 1-phenoxathiin-2-ylethanone Chemical compound C1=CC=C2SC3=CC(C(=O)C)=CC=C3OC2=C1 NTIVMTODXGIOHE-UHFFFAOYSA-N 0.000 description 2
SMHWYMFRUDJGJF-UHFFFAOYSA-N 10,10-dioxo-4-(2h-tetrazol-5-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1C=1N=NNN=1 SMHWYMFRUDJGJF-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NKSIOGJHWXLQRJ-UHFFFAOYSA-N 2-[5-(9,10,10-trioxothioxanthen-3-yl)tetrazol-2-yl]acetic acid Chemical compound OC(=O)CN1N=NC(C=2C=C3S(=O)(=O)C4=CC=CC=C4C(=O)C3=CC=2)=N1 NKSIOGJHWXLQRJ-UHFFFAOYSA-N 0.000 description 2
XZOCJJIQHMPYBF-UHFFFAOYSA-N 2-methyl-8-(2h-tetrazol-5-yl)phenoxathiine 10,10-dioxide Chemical compound C1=C2S(=O)(=O)C3=CC(C)=CC=C3OC2=CC=C1C=1N=NNN=1 XZOCJJIQHMPYBF-UHFFFAOYSA-N 0.000 description 2
QSZCSMSUKRGFOL-UHFFFAOYSA-N 3-(2-methyltetrazol-5-yl)-10,10-dioxothioxanthen-9-one Chemical compound CN1N=NC(C=2C=C3S(=O)(=O)C4=CC=CC=C4C(=O)C3=CC=2)=N1 QSZCSMSUKRGFOL-UHFFFAOYSA-N 0.000 description 2
HOKGUHQUCLLXOG-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)thianthrene 5,5-dioxide Chemical compound C1=C2S(=O)(=O)C3=CC=CC=C3SC2=CC=C1C1=NN=NN1 HOKGUHQUCLLXOG-UHFFFAOYSA-N 0.000 description 2
ZLOILRDPUMCBAR-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-4-carbonitrile Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1C#N ZLOILRDPUMCBAR-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
WFQWCLKNTPDVJP-UHFFFAOYSA-N phenoxathiine-2-carboxylic acid Chemical compound C1=CC=C2SC3=CC(C(=O)O)=CC=C3OC2=C1 WFQWCLKNTPDVJP-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NQDUNKLNHWXHTK-UHFFFAOYSA-N 10,10-dioxo-9h-thioxanthene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3CC2=C1 NQDUNKLNHWXHTK-UHFFFAOYSA-N 0.000 description 1
UMXYXYRQHGEFGZ-UHFFFAOYSA-N 10,10-dioxophenoxathiine-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 UMXYXYRQHGEFGZ-UHFFFAOYSA-N 0.000 description 1
ITTPKTWJMJMKEW-UHFFFAOYSA-N 10,10-dioxothianthrene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3SC2=C1 ITTPKTWJMJMKEW-UHFFFAOYSA-N 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
UJTTUBGLVPQECG-UHFFFAOYSA-N 2-methyl-10,10-dioxo-6-(2h-tetrazol-5-yl)thioxanthen-9-one Chemical compound C=1C(C)=CC=C(S(C2=C3)(=O)=O)C=1C(=O)C2=CC=C3C=1N=NNN=1 UJTTUBGLVPQECG-UHFFFAOYSA-N 0.000 description 1
PQKVAMBSIOBTTB-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)dibenzothiophene 5,5-dioxide Chemical compound C1=C2S(=O)(=O)C3=CC=CC=C3C2=CC=C1C1=NN=NN1 PQKVAMBSIOBTTB-UHFFFAOYSA-N 0.000 description 1
WNBDHEDHQVVCDL-UHFFFAOYSA-N 3-[2-[3-(dimethylamino)propyl]tetrazol-5-yl]-10,10-dioxothioxanthen-9-one Chemical compound CN(C)CCCN1N=NC(C=2C=C3S(=O)(=O)C4=CC=CC=C4C(=O)C3=CC=2)=N1 WNBDHEDHQVVCDL-UHFFFAOYSA-N 0.000 description 1
QIJPPXRXUUHIDI-UHFFFAOYSA-N 3-[5-(9,10,10-trioxothioxanthen-3-yl)tetrazol-1-yl]propanoic acid Chemical compound OC(=O)CCN1N=NN=C1C1=CC=C(C(=O)C=2C(=CC=CC=2)S2(=O)=O)C2=C1 QIJPPXRXUUHIDI-UHFFFAOYSA-N 0.000 description 1
LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
NQWYLTBMVTXHIF-UHFFFAOYSA-N 3-phenyl-4-sulfanylcarbonylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(O)=S)C(C=2C=CC=CC=2)=C1 NQWYLTBMVTXHIF-UHFFFAOYSA-N 0.000 description 1
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HOJKPKWYXUGOEZ-UHFFFAOYSA-N 7-methyl-9,10,10-trioxothioxanthene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2S(=O)(=O)C3=CC=C(C)C=C3C(=O)C2=C1 HOJKPKWYXUGOEZ-UHFFFAOYSA-N 0.000 description 1
HGLRPMVUMPVQCV-UHFFFAOYSA-N 8-methyl-10,10-dioxophenoxathiine-2-carbonitrile Chemical compound C1=C(C#N)C=C2S(=O)(=O)C3=CC(C)=CC=C3OC2=C1 HGLRPMVUMPVQCV-UHFFFAOYSA-N 0.000 description 1
YSBGMLKPMDKCPB-UHFFFAOYSA-N 8-methyl-10,10-dioxophenoxathiine-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2S(=O)(=O)C3=CC(C)=CC=C3OC2=C1 YSBGMLKPMDKCPB-UHFFFAOYSA-N 0.000 description 1
HWWLQYBCAODZCA-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-4-carboxylic acid Chemical compound O=C1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2C(=O)O HWWLQYBCAODZCA-UHFFFAOYSA-N 0.000 description 1
RCIBZULWCFTTJK-UHFFFAOYSA-N 9-oxothioxanthene-4-carbonitrile Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1C#N RCIBZULWCFTTJK-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000003341 Bronsted base Substances 0.000 description 1
ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
241000700159 Rattus Species 0.000 description 1
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206010040914 Skin reaction Diseases 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
230000002862 amidating effect Effects 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001411 amidrazones Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 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
239000008187 granular material Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
150000002463 imidates Chemical group 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229960002657 orciprenaline Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
230000035483 skin reaction Effects 0.000 description 1
231100000430 skin reaction Toxicity 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
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
YAOMBFIYBNUKHD-UHFFFAOYSA-N thianthrene 5,5-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3SC2=C1 YAOMBFIYBNUKHD-UHFFFAOYSA-N 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/12—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH713973A 1972-05-19 1973-05-18 CH616423A5 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB2380572		1972-05-19
GB4142972		1972-09-06
GB2117473*[A GB1447031A (en)	1972-05-19	1973-05-04	Tricyclic sulphones and pharmaceutical compositions containing them

Publications (1)

Publication Number	Publication Date
CH616423A5 true CH616423A5 (es)	1980-03-31

Family

ID=27257983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH713973A CH616423A5 (es)	1972-05-19	1973-05-18

Country Status (16)

Country	Link
US (1)	US3905989A (es)
JP (1)	JPS4948657A (es)
AR (4)	AR210237A1 (es)
AT (1)	AT336011B (es)
CA (1)	CA1024987A (es)
CH (1)	CH616423A5 (es)
DD (1)	DD108539A5 (es)
DE (1)	DE2325300A1 (es)
ES (1)	ES414888A1 (es)
FR (3)	FR2185407B1 (es)
GB (1)	GB1447031A (es)
IE (2)	IE37645B1 (es)
IL (3)	IL50000A (es)
LU (1)	LU67622A1 (es)
NL (1)	NL7306958A (es)
SE (1)	SE7604471L (es)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4012517A (en) *	1975-01-24	1977-03-15	Burroughs Wellcome Co.	Compositions and treatment
SE7600689L (sv) *	1975-01-24	1976-07-26	Wellcome Found	Farmakologiskt aktiva kompositioner
CH628343A5 (en) *	1977-03-24	1982-02-26	Sandoz Ag	Process for preparing thioxanthones
US4536507A (en) *	1977-07-26	1985-08-20	Merck & Co., Inc.	Prostaglandin antagonists
US4221800A (en) *	1977-12-23	1980-09-09	Miles Laboratories, Inc.	Cycloalkenochromone
FR2419282A1 (fr) *	1978-03-09	1979-10-05	Labaz	Nouveau derive de benzonitrile, son procede de preparation et son application
US4394515A (en) *	1978-06-23	1983-07-19	Merck & Co., Inc.	10,11-Dihydro-11-oxodibenzo[b,f]thiepin compounds
CH640849A5 (de) *	1979-05-18	1984-01-31	Ciba Geigy Ag	Thioxanthoncarbonsaeureester, -thioester und -amide.
US4432986A (en) *	1979-06-18	1984-02-21	Riker Laboratories, Inc.	Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof
NL8005946A (nl) *	1979-11-02	1981-06-01	Hoffmann La Roche	Middelen tegen vetzucht en verhoogde vetspiegel.
US4237160A (en) *	1979-11-27	1980-12-02	Merck Sharp & Dohme (I.A.) Corp.	3-Hydroxymethyldibenzo[b,f]thiepins as prostaglandin antagonists
US4500540A (en) *	1979-12-26	1985-02-19	Hoffmann-La Roche Inc.	Thromboxane synthase inhibitors as insulin lowering agents and antionbesity agents
US4731363A (en) *	1979-12-26	1988-03-15	Hoffmann-La Roche Inc.	Thromboxane synthase inhibitors as insulin lowering agents and antiobesity agents
JPS5716821A (en) *	1980-07-04	1982-01-28	Yoshitomi Pharmaceut Ind Ltd	Remedy for disease due to immunological dysfunction
US4377579A (en) *	1981-12-03	1983-03-22	Minnesota Mining And Manufacturing Company	N-(Tetrazol-5-yl)phenazine-1-carboxamides
US4535171A (en) *	1982-11-18	1985-08-13	Merck Frosst Canada, Inc.	Dibenzo[b,f]thiepin-3-carboxaldehydes as prostaglandin antagonists
EP0150891A1 (en) *	1984-01-05	1985-08-07	The Wellcome Foundation Limited	Tricyclic compounds, processes for their preparation, compositions containing such compounds and their use in medicine
GB8400202D0 (en) *	1984-01-05	1984-02-08	Wellcome Found	Tricyclic compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3096343A (en) *	1960-07-20	1963-07-02	Du Pont	Method for isolating aromatic carboxylic acids
US3555043A (en) *	1969-02-17	1971-01-12	Sterling Drug Inc	Tertiary-amino-lower-alkoxy-9-benzylxanthenes and thioxanthenes
US3642997A (en) *	1969-06-25	1972-02-15	Merck & Co Inc	Tricyclic carboxylic acids in the treatment of inflammation
BE759292A (fr) *	1969-11-27	1971-05-24	Allen & Hanburys Ltd	Derives de xanthone, leur preparation et leur emploi

1973
- 1973-05-04 GB GB2117473*[A patent/GB1447031A/en not_active Expired
- 1973-05-18 IL IL7350000A patent/IL50000A/xx unknown
- 1973-05-18 CA CA171,774A patent/CA1024987A/en not_active Expired
- 1973-05-18 JP JP48055454A patent/JPS4948657A/ja active Pending
- 1973-05-18 LU LU67622A patent/LU67622A1/xx unknown
- 1973-05-18 IE IE795/73A patent/IE37645B1/xx unknown
- 1973-05-18 DD DD170909A patent/DD108539A5/xx unknown
- 1973-05-18 AR AR248104A patent/AR210237A1/es active
- 1973-05-18 NL NL7306958A patent/NL7306958A/xx not_active Application Discontinuation
- 1973-05-18 IL IL7342311A patent/IL42311A/xx unknown
- 1973-05-18 AT AT435573A patent/AT336011B/de not_active IP Right Cessation
- 1973-05-18 US US361523A patent/US3905989A/en not_active Expired - Lifetime
- 1973-05-18 CH CH713973A patent/CH616423A5/de not_active IP Right Cessation
- 1973-05-18 IE IE2480/76A patent/IE37646B1/xx unknown
- 1973-05-18 ES ES414888A patent/ES414888A1/es not_active Expired
- 1973-05-18 DE DE2325300A patent/DE2325300A1/de active Pending
- 1973-05-21 FR FR7318299A patent/FR2185407B1/fr not_active Expired
1974
- 1974-08-10 AR AR255012A patent/AR210245A1/es active
1975
- 1975-07-16 AR AR259624A patent/AR209311A1/es active
1976
- 1976-02-17 FR FR7604263A patent/FR2300088A1/fr active Granted
- 1976-02-17 FR FR7604262A patent/FR2293198A1/fr active Granted
- 1976-04-15 SE SE7604471A patent/SE7604471L/xx unknown
- 1976-07-08 IL IL7650000A patent/IL50000A0/xx unknown
- 1976-08-06 AR AR259185D patent/AR206633A1/es active

Also Published As

Publication number	Publication date
US3905989A (en)	1975-09-16
AR210245A1 (es)	1977-07-15
CA1024987A (en)	1978-01-24
IL50000A0 (en)	1976-09-30
AR210237A1 (es)	1977-07-15
LU67622A1 (es)	1973-11-23
AT336011B (de)	1977-04-12
IL42311A (en)	1978-03-10
FR2293198B1 (es)	1979-06-29
IL42311A0 (en)	1973-07-30
AR209311A1 (es)	1977-04-15
DD108539A5 (es)	1974-09-20
JPS4948657A (es)	1974-05-11
GB1447031A (en)	1976-08-25
ES414888A1 (es)	1976-06-01
NL7306958A (es)	1973-11-21
DE2325300A1 (de)	1973-12-20
FR2293198A1 (fr)	1976-07-02
ATA435573A (de)	1976-08-15
FR2185407B1 (es)	1977-08-19
AU5595973A (en)	1974-11-21
IE37646B1 (en)	1977-09-14
SE7604471L (sv)	1976-04-15
AR206633A1 (es)	1976-08-06
IE37645B1 (en)	1977-09-14
IL50000A (en)	1978-03-10
FR2300088B1 (es)	1980-04-25
FR2300088A1 (fr)	1976-09-03
IE37645L (en)	1973-11-19
FR2185407A1 (es)	1974-01-04

Publication	Publication Date	Title
EP0013376B1 (de)	1982-05-19	Ein Isoxazolderivat, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Mittel
EP0149242B1 (de)	1990-10-31	1-(2-Hydroxyaryl)-alkan-1-on-oxime, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
CH616423A5 (es)	1980-03-31
CH625243A5 (es)	1981-09-15
EP0127726B1 (de)	1987-08-26	Hydroxamsäuren, ihre Herstellung und ihre Verwendung in pharmazeutischen Mitteln
EP0025192A2 (de)	1981-03-18	Substituierte Oxirancarbonsäuren, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende Arzneimittel
DD251126A1 (de)	1987-11-04	Verfahren zur herstellung neuer 2-arylsulfonamido-benzo- und -acetophenone und deren oxime, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE2931418C2 (es)	1989-06-29
DE2846931A1 (de)	1979-05-10	Tetrazol-derivate
AT371461B (de)	1983-06-27	Verfahren zur herstellung neuer benzopyranderivate und deren salze
DE69014798T2 (de)	1995-04-27	Thionaphthalen-derivate, verfahren zur herstellung und antiallergisches mittel daraus.
EP0014847A1 (de)	1980-09-03	Pyrazolderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
DE2344799A1 (de)	1974-03-21	Schwefelhaltige tricyclische verbindungen und diese enthaltende arzneimittel
DE3035688C2 (es)	1990-05-17
DE2307828A1 (de)	1973-08-23	(4-benzothiazolyl)-phenylessigsaeuren
DE2319834C3 (de)	1983-02-03	Derivate von 2-Carboxy-pyrazin-4-oxiden, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE1960910A1 (de)	1970-07-09	Neue Benzylidenamino-oxyalkylcarbonsaeuren und Carbonsaeurederivate
CH649289A5 (de)	1985-05-15	2-pyridyl- und 2-pyrimidylaminobenzoesaeuren.
DE2253914A1 (de)	1973-05-10	Neue chromonderivate und verfahren zu ihrer herstellung
DE2734270C2 (es)	1990-06-21
EP0442348B1 (de)	1996-07-17	Neue Imidazolverbindungen, Verfahren zu deren Herstellung, Arzneimittel auf Basis dieser Verbindungen sowie einige Zwischenprodukte
DE3034005C2 (de)	1982-12-09	Indolessigsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CH626613A5 (en)	1981-11-30	Process for the preparation of polycyclic compounds containing at least one tetrazole ring
DE2525164C2 (de)	1986-10-16	m-Phenylendioxamsäurediester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
DE3717079A1 (de)	1988-01-07	3-(hydroxymethyl)-isochinolinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel sowie 3-(acyloxymethyl)-isochinolinderivate und verfahren zur herstellung der letzteren

Legal Events

Date	Code	Title	Description
1987-01-30	PL	Patent ceased
2024-10-31	PL	Patent ceased