SE124739C1 - - Google Patents
Info
- Publication number
- SE124739C1 SE124739C1 SE124739DA SE124739C1 SE 124739 C1 SE124739 C1 SE 124739C1 SE 124739D A SE124739D A SE 124739DA SE 124739 C1 SE124739 C1 SE 124739C1
- Authority
- SE
- Sweden
- Prior art keywords
- process according
- group
- condensed
- para
- substituent
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 29
- -1 benzo sulfonic acid derivative Chemical class 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical class C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 9
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 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 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229960001544 sulfathiazole Drugs 0.000 claims description 4
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- APUVABKNTSHIJM-UHFFFAOYSA-N 4-[bis[4-(dimethylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 APUVABKNTSHIJM-UHFFFAOYSA-N 0.000 claims description 2
- PPGSUPFDLFLUAL-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonamide Chemical compound CC1=CC(N)=CC=C1S(N)(=O)=O PPGSUPFDLFLUAL-UHFFFAOYSA-N 0.000 claims description 2
- QOWLTTCFQDJQHQ-UHFFFAOYSA-N 4-amino-2-phenylbenzenesulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C(C=2C=CC=CC=2)=C1 QOWLTTCFQDJQHQ-UHFFFAOYSA-N 0.000 claims description 2
- IVKMZPOWNVXFFH-UHFFFAOYSA-N 4-benzhydrylaniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 IVKMZPOWNVXFFH-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- IYYLZMUMLWEPGS-UHFFFAOYSA-N n-methyl-1,1,1-triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NC)C1=CC=CC=C1 IYYLZMUMLWEPGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- CGRKCGWEOIQFRD-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonylazanide Chemical compound [Na+].NC1=CC=C(S([NH-])(=O)=O)C=C1 CGRKCGWEOIQFRD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- TVAAWIWWRZDCBU-UHFFFAOYSA-N 4-[bis[4-(dimethylamino)phenyl]methyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N)C=C1 TVAAWIWWRZDCBU-UHFFFAOYSA-N 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- ABBQGOCHXSPKHJ-WUKNDPDISA-N prontosil Chemical compound NC1=CC(N)=CC=C1\N=N\C1=CC=C(S(N)(=O)=O)C=C1 ABBQGOCHXSPKHJ-WUKNDPDISA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE124739T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE124739C1 true SE124739C1 (enExample) | 1949-01-01 |
Family
ID=41923550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE124739D SE124739C1 (enExample) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE124739C1 (enExample) |
-
0
- SE SE124739D patent/SE124739C1/sv unknown
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