SE204141C1 - - Google Patents
Info
- Publication number
- SE204141C1 SE204141C1 SE204141DA SE204141C1 SE 204141 C1 SE204141 C1 SE 204141C1 SE 204141D A SE204141D A SE 204141DA SE 204141 C1 SE204141 C1 SE 204141C1
- Authority
- SE
- Sweden
- Prior art keywords
- phentiazine
- aniline
- phenyl
- sulfur
- benzene
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 M-sec-butyl-mercapto-aniline Chemical compound 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- BZPGKPLLPRDLTC-UHFFFAOYSA-N 3-(2-methylpropylsulfanyl)-N-phenylaniline Chemical compound C(C(C)C)SC=1C=C(C=CC1)NC1=CC=CC=C1 BZPGKPLLPRDLTC-UHFFFAOYSA-N 0.000 description 2
- GKLFDWGXDPXYFM-UHFFFAOYSA-N 3-benzylsulfanyl-N-phenylaniline Chemical compound C(SC1=CC=CC(NC2=CC=CC=C2)=C1)C1=CC=CC=C1 GKLFDWGXDPXYFM-UHFFFAOYSA-N 0.000 description 2
- YNHGMBTXSRJGLC-UHFFFAOYSA-N 3-ethylsulfanyl-n-phenylaniline Chemical compound CCSC1=CC=CC(NC=2C=CC=CC=2)=C1 YNHGMBTXSRJGLC-UHFFFAOYSA-N 0.000 description 2
- NGTRZJDYCCOXBA-UHFFFAOYSA-N 3-methylsulfanyl-n-phenylaniline Chemical compound CSC1=CC=CC(NC=2C=CC=CC=2)=C1 NGTRZJDYCCOXBA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DBVMVLJJUKDKPU-UHFFFAOYSA-N N-phenyl-3-propan-2-ylsulfanylaniline Chemical compound CC(C)SC1=CC=CC(NC2=CC=CC=C2)=C1 DBVMVLJJUKDKPU-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- XXBJOUVPMYFEMP-UHFFFAOYSA-N 1-nitro-3-propan-2-ylsulfanylbenzene Chemical compound CC(C)SC1=CC=CC([N+]([O-])=O)=C1 XXBJOUVPMYFEMP-UHFFFAOYSA-N 0.000 description 1
- ISVGOYORMPENJM-UHFFFAOYSA-N 2-(3-benzylsulfanylanilino)benzoic acid Chemical compound C(C1=CC=CC=C1)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 ISVGOYORMPENJM-UHFFFAOYSA-N 0.000 description 1
- LIWNFNNKPBGCFM-UHFFFAOYSA-N 2-(3-ethylsulfanylanilino)benzoic acid Chemical compound CCSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 LIWNFNNKPBGCFM-UHFFFAOYSA-N 0.000 description 1
- JLVZKULKBLUFIY-UHFFFAOYSA-N 2-(3-methylsulfanylanilino)benzoic acid Chemical compound CSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 JLVZKULKBLUFIY-UHFFFAOYSA-N 0.000 description 1
- RMMIRCPZDWCSMD-UHFFFAOYSA-N 2-(3-propan-2-ylsulfanylanilino)benzoic acid Chemical compound C(C)(C)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 RMMIRCPZDWCSMD-UHFFFAOYSA-N 0.000 description 1
- GNFLEVKVWSBFBQ-UHFFFAOYSA-N 2-nitro-6-propylbenzenethiol Chemical compound C(CC)C=1C(=C(C=CC1)[N+](=O)[O-])S GNFLEVKVWSBFBQ-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- DOJQBZDNLHHVJE-UHFFFAOYSA-N 3-(2-methylpropylsulfanyl)aniline Chemical compound CC(C)CSC1=CC=CC(N)=C1 DOJQBZDNLHHVJE-UHFFFAOYSA-N 0.000 description 1
- XVUKOTZEXLIZIB-UHFFFAOYSA-N 3-benzylsulfanylaniline Chemical compound NC1=CC=CC(SCC=2C=CC=CC=2)=C1 XVUKOTZEXLIZIB-UHFFFAOYSA-N 0.000 description 1
- LEUKPJKOYBCWGE-UHFFFAOYSA-N 3-butylsulfanyl-N-phenylaniline Chemical compound C(CCC)SC=1C=C(C=CC1)NC1=CC=CC=C1 LEUKPJKOYBCWGE-UHFFFAOYSA-N 0.000 description 1
- KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
- LQHCJNXJRJAKIC-UHFFFAOYSA-N 3-propan-2-ylsulfanylaniline Chemical compound CC(C)SC1=CC=CC(N)=C1 LQHCJNXJRJAKIC-UHFFFAOYSA-N 0.000 description 1
- PKKKSXIPDFGVKI-UHFFFAOYSA-N CCC1=CC=CC(NS)=C1 Chemical compound CCC1=CC=CC(NS)=C1 PKKKSXIPDFGVKI-UHFFFAOYSA-N 0.000 description 1
- 101100373139 Caenorhabditis elegans mig-14 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 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 1
- BZGGXHBFYOQDON-UHFFFAOYSA-N N-phenyl-3-propylsulfanylaniline Chemical compound C(CC)SC=1C=C(C=CC1)NC1=CC=CC=C1 BZGGXHBFYOQDON-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE204141T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE204141C1 true SE204141C1 (da) | 1965-01-01 |
Family
ID=41987739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE204141D SE204141C1 (da) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE204141C1 (da) |
-
0
- SE SE204141D patent/SE204141C1/sv unknown
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