CH617432A5 - Process for the preparation of sulphur-containing heterotricyclic compounds - Google Patents
Process for the preparation of sulphur-containing heterotricyclic compounds Download PDFInfo
- Publication number
- CH617432A5 CH617432A5 CH1282673A CH1282673A CH617432A5 CH 617432 A5 CH617432 A5 CH 617432A5 CH 1282673 A CH1282673 A CH 1282673A CH 1282673 A CH1282673 A CH 1282673A CH 617432 A5 CH617432 A5 CH 617432A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- group
- compounds
- alkyl
- salts
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 68
- 238000000034 method Methods 0.000 title claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 8
- 239000005864 Sulphur Substances 0.000 title 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 24
- -1 5-tetrazolyl Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003375 sulfoxide group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000002685 pulmonary effect Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229960001340 histamine Drugs 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 claims 1
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 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 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 206010040914 Skin reaction Diseases 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 230000002052 anaphylactic effect Effects 0.000 claims 1
- 230000036783 anaphylactic response Effects 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 210000000038 chest Anatomy 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 210000003630 histaminocyte Anatomy 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 150000003139 primary aliphatic amines Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 230000035483 skin reaction Effects 0.000 claims 1
- 231100000430 skin reaction Toxicity 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 125000004001 thioalkyl group Chemical group 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 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
- 239000000706 filtrate Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- NSIYJWMAAOULCQ-UHFFFAOYSA-N 10-oxophenoxathiine-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2S(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 NSIYJWMAAOULCQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 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
- 150000003536 tetrazoles Chemical class 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 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
- 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 3
- CSRUXJVRQRNTBL-UHFFFAOYSA-N 7-chloro-9h-thioxanthene-3-carboxylic acid Chemical compound ClC1=CC=C2SC3=CC(C(=O)O)=CC=C3CC2=C1 CSRUXJVRQRNTBL-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
- 239000004604 Blowing Agent Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000013543 active substance Substances 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 2
- 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000003341 Bronsted base Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical group ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 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
- 230000000172 allergic effect Effects 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 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
- 239000002243 precursor Substances 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 2
- NYVGTLXTOJKHJN-UHFFFAOYSA-N thianthrene 5-oxide Chemical class C1=CC=C2S(=O)C3=CC=CC=C3SC2=C1 NYVGTLXTOJKHJN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000005075 thioxanthenes Chemical class 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
- 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 1
- XLKTXBRNWCHYAS-UHFFFAOYSA-N 1-thianthren-2-ylethanone Chemical compound C1=CC=C2SC3=CC(C(=O)C)=CC=C3SC2=C1 XLKTXBRNWCHYAS-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- HQARDVLSJLCFBA-UHFFFAOYSA-N 4-[(4-aminophenyl)carbamoyl]-1h-imidazole-5-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)C1=C(C(O)=O)NC=N1 HQARDVLSJLCFBA-UHFFFAOYSA-N 0.000 description 1
- ASXIDTTVFXHPPZ-UHFFFAOYSA-N 4-carbamothioyl-1-chloro-5-phenylcyclohexa-2,4-diene-1-carboxamide Chemical compound C1=CC(C(=O)N)(Cl)CC(C=2C=CC=CC=2)=C1C(N)=S ASXIDTTVFXHPPZ-UHFFFAOYSA-N 0.000 description 1
- ZIYILGYCQDBDIZ-UHFFFAOYSA-N 4-chloro-2-phenylsulfanylcyclohexa-1,5-diene-1,4-dicarbonitrile Chemical compound C1=CC(Cl)(C#N)CC(SC=2C=CC=CC=2)=C1C#N ZIYILGYCQDBDIZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 230000003385 bacteriostatic effect Effects 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
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NAVUESYOIIFRAL-UHFFFAOYSA-N dibenzothiophene-3,7-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C=C3SC2=C1 NAVUESYOIIFRAL-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000024711 extrinsic asthma Diseases 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 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
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 238000001665 trituration Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 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 |
|---|---|
| CH617432A5 true CH617432A5 (en) | 1980-05-30 |
Family
ID=26263961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1282673A CH617432A5 (en) | 1972-09-06 | 1973-09-06 | Process for the preparation of sulphur-containing heterotricyclic compounds |
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 |
| IL43161A (en) | 1978-07-31 |
| JPS4992062A (enrdf_load_stackoverflow) | 1974-09-03 |
| DE2344800A1 (de) | 1974-03-21 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |