DE2344800A1 - Schwefelhaltige tricyclische verbindungen und diese enthaltende pharmazeutische zubereitungen - Google Patents
Schwefelhaltige tricyclische verbindungen und diese enthaltende pharmazeutische zubereitungenInfo
- Publication number
- DE2344800A1 DE2344800A1 DE19732344800 DE2344800A DE2344800A1 DE 2344800 A1 DE2344800 A1 DE 2344800A1 DE 19732344800 DE19732344800 DE 19732344800 DE 2344800 A DE2344800 A DE 2344800A DE 2344800 A1 DE2344800 A1 DE 2344800A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- formula
- tetrazolyl
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 114
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 43
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 239000011593 sulfur Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- -1 5-tetrazolyl Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004442 acylamino group Chemical group 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 25
- 125000004001 thioalkyl group Chemical group 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 20
- 125000003375 sulfoxide group Chemical group 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 150000003462 sulfoxides Chemical class 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052727 yttrium Inorganic materials 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 210000004072 lung Anatomy 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- QVSRVLMLSCHVOR-UHFFFAOYSA-N 9,10-dioxothioxanthene-3-carboxylic acid Chemical compound C(=O)(O)C=1C=CC=2C(C3=CC=CC=C3S(C2C1)=O)=O QVSRVLMLSCHVOR-UHFFFAOYSA-N 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 229910052945 inorganic sulfide Inorganic materials 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- LRALZUMOPVTKMO-UHFFFAOYSA-N 7-nitro-5,10-dioxothianthrene-1-carboxylic acid Chemical compound O=S1C2=CC=C([N+]([O-])=O)C=C2S(=O)C2=C1C(C(=O)O)=CC=C2 LRALZUMOPVTKMO-UHFFFAOYSA-N 0.000 claims 1
- 241000272517 Anseriformes Species 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 150000003536 tetrazoles Chemical class 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 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
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 210000001508 eye Anatomy 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- SEQQECSHITUZQZ-UHFFFAOYSA-N phenoxathiine-2-carbonitrile Chemical compound C1=CC=C2SC3=CC(C#N)=CC=C3OC2=C1 SEQQECSHITUZQZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003380 propellant Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QJCZURPWFJGEED-UHFFFAOYSA-N 1-chloro-5-phenyl-4-sulfanylcarbonylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(C(=O)O)(Cl)CC(C=2C=CC=CC=2)=C1C(O)=S QJCZURPWFJGEED-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KAQXLLBJTJCNHD-UHFFFAOYSA-N 5-(7-chloro-9h-thioxanthen-3-yl)-2h-tetrazole Chemical compound C=1C=C2CC3=CC(Cl)=CC=C3SC2=CC=1C1=NN=NN1 KAQXLLBJTJCNHD-UHFFFAOYSA-N 0.000 description 3
- IBRSIERVSWSOKL-UHFFFAOYSA-N 5-phenoxathiin-2-yl-2h-tetrazole Chemical compound C=1C=C2OC3=CC=CC=C3SC2=CC=1C1=NN=NN1 IBRSIERVSWSOKL-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
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 3
- NYVGTLXTOJKHJN-UHFFFAOYSA-N thianthrene 5-oxide Chemical class C1=CC=C2S(=O)C3=CC=CC=C3SC2=C1 NYVGTLXTOJKHJN-UHFFFAOYSA-N 0.000 description 3
- BLJIAZIZIXSNJZ-UHFFFAOYSA-N thianthrene-2-carboxylic acid Chemical compound C1=CC=C2SC3=CC(C(=O)O)=CC=C3SC2=C1 BLJIAZIZIXSNJZ-UHFFFAOYSA-N 0.000 description 3
- 150000005075 thioxanthenes Chemical class 0.000 description 3
- KZJDSILKHOJSFN-UHFFFAOYSA-N 1-(8-acetylphenoxathiin-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=C2SC3=CC(C(=O)C)=CC=C3OC2=C1 KZJDSILKHOJSFN-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
- FVHRCCOBSLPTMY-UHFFFAOYSA-N 10-oxophenoxathiine-2-carboxylic acid Chemical compound C1=CC=C2S(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 FVHRCCOBSLPTMY-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- UOSBUEIRGJBVCK-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)phenoxathiine 10-oxide Chemical compound C1=C2S(=O)C3=CC=CC=C3OC2=CC=C1C=1N=NNN=1 UOSBUEIRGJBVCK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGRLSJHVYJVFDM-UHFFFAOYSA-N 2-chloro-6-(2h-tetrazol-5-yl)-9h-thioxanthene 10-oxide Chemical compound C=1C(Cl)=CC=C(S(C2=C3)=O)C=1CC2=CC=C3C=1N=NNN=1 NGRLSJHVYJVFDM-UHFFFAOYSA-N 0.000 description 2
- YNPQWZYNYNGSTA-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)thianthrene 5-oxide Chemical compound C1=C2S(=O)C3=CC=CC=C3SC2=CC=C1C1=NN=NN1 YNPQWZYNYNGSTA-UHFFFAOYSA-N 0.000 description 2
- MJJFOHAMYJAHKV-UHFFFAOYSA-N 7-chloro-9h-thioxanthene-3-carbonitrile Chemical compound N#CC1=CC=C2CC3=CC(Cl)=CC=C3SC2=C1 MJJFOHAMYJAHKV-UHFFFAOYSA-N 0.000 description 2
- KAVCRNNWZSTKGM-UHFFFAOYSA-N 9-oxothioxanthene-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC=C(C(=O)O)C=C3SC2=C1 KAVCRNNWZSTKGM-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000009619 Gattermann reaction Methods 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
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- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical class CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 150000002823 nitrates Chemical class 0.000 description 1
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- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 238000005580 one pot reaction Methods 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
- 230000036961 partial effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZESLIAUQVGLCIA-UHFFFAOYSA-N phenoxathiine 10-oxide Chemical class C1=CC=C2S(=O)C3=CC=CC=C3OC2=C1 ZESLIAUQVGLCIA-UHFFFAOYSA-N 0.000 description 1
- BRXPROMQNRKVQC-UHFFFAOYSA-N phenoxathiine-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC3=CC(C(=O)O)=CC=C3OC2=C1 BRXPROMQNRKVQC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- CEJYDWOCESGOJP-UHFFFAOYSA-N thianthrene 5,10-dioxide Chemical class C1=CC=C2S(=O)C3=CC=CC=C3S(=O)C2=C1 CEJYDWOCESGOJP-UHFFFAOYSA-N 0.000 description 1
- 150000005029 thianthrenes Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- 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
- 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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4143472A GB1458186A (en) | 1972-09-06 | 1972-09-06 | Oxides of sulphur-containing tricyclic compounds methods for their preparation and compositions containing them |
| GB3895173 | 1973-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2344800A1 true DE2344800A1 (de) | 1974-03-21 |
Family
ID=26263961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732344800 Pending DE2344800A1 (de) | 1972-09-06 | 1973-09-05 | Schwefelhaltige tricyclische verbindungen und diese enthaltende pharmazeutische zubereitungen |
Country Status (10)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642997A (en) * | 1969-06-25 | 1972-02-15 | Merck & Co Inc | Tricyclic carboxylic acids in the treatment of inflammation |
| NL7008628A (enrdf_load_stackoverflow) * | 1969-06-25 | 1970-12-29 | ||
| BE793954A (fr) * | 1972-07-19 | 1973-07-12 | Syntex Corp | Acides thioxanthone-carboxyliques et leurs derives |
-
1972
- 1972-09-06 GB GB4143472A patent/GB1458186A/en not_active Expired
-
1973
- 1973-09-05 ES ES418492A patent/ES418492A1/es not_active Expired
- 1973-09-05 DE DE19732344800 patent/DE2344800A1/de active Pending
- 1973-09-05 IL IL43161A patent/IL43161A/xx unknown
- 1973-09-06 CA CA180,430A patent/CA1027953A/en not_active Expired
- 1973-09-06 NL NL7312252A patent/NL7312252A/xx not_active Application Discontinuation
- 1973-09-06 IE IE1591/73A patent/IE39567B1/xx unknown
- 1973-09-06 CH CH1282673A patent/CH617432A5/de not_active IP Right Cessation
- 1973-09-06 JP JP48100726A patent/JPS4992062A/ja active Pending
- 1973-09-06 FR FR7332119A patent/FR2199469B1/fr not_active Expired
-
1976
- 1976-01-14 FR FR7600806A patent/FR2289183A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1458186A (en) | 1976-12-08 |
| NL7312252A (enrdf_load_stackoverflow) | 1974-03-08 |
| CH617432A5 (en) | 1980-05-30 |
| IL43161A (en) | 1978-07-31 |
| JPS4992062A (enrdf_load_stackoverflow) | 1974-09-03 |
| ES418492A1 (es) | 1976-07-16 |
| FR2199469B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| CA1027953A (en) | 1978-03-14 |
| IL43161A0 (en) | 1973-11-28 |
| IE39567B1 (en) | 1978-11-08 |
| FR2289183A1 (fr) | 1976-05-28 |
| FR2199469A1 (enrdf_load_stackoverflow) | 1974-04-12 |
| FR2289183B1 (enrdf_load_stackoverflow) | 1978-08-18 |
| IE39567L (en) | 1974-03-06 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination |