CA2105665C - Derives diphenylthiazole - Google Patents
Derives diphenylthiazoleInfo
- Publication number
- CA2105665C CA2105665C CA 2105665 CA2105665A CA2105665C CA 2105665 C CA2105665 C CA 2105665C CA 2105665 CA2105665 CA 2105665 CA 2105665 A CA2105665 A CA 2105665A CA 2105665 C CA2105665 C CA 2105665C
- Authority
- CA
- Canada
- Prior art keywords
- group
- diphenylthiazole
- compound
- halogenated
- trifluoromethanesulfonylamino
- 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.)
- Expired - Fee Related
Links
- MIECVJDZXBUVSN-UHFFFAOYSA-N 2,4-diphenyl-1,3-thiazole Chemical class C=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MIECVJDZXBUVSN-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 3
- -1 4-chlorobenzenesulfonyl group Chemical group 0.000 claims description 18
- LQSAEPZCYJFJQN-UHFFFAOYSA-N n-(4,5-diphenyl-1,3-thiazol-2-yl)-1,1,1-trifluoromethanesulfonamide Chemical compound S1C(NS(=O)(=O)C(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LQSAEPZCYJFJQN-UHFFFAOYSA-N 0.000 claims description 2
- AQDGFJWNNWFNSV-UHFFFAOYSA-N 1,1,1-trifluoro-n-[4-(4-methoxyphenyl)-5-phenyl-1,3-thiazol-2-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)SC(NS(=O)(=O)C(F)(F)F)=N1 AQDGFJWNNWFNSV-UHFFFAOYSA-N 0.000 claims 1
- NQCZJQNFGCNRND-UHFFFAOYSA-N 1,1,1-trifluoro-n-[5-(4-fluorophenyl)-4-phenyl-1,3-thiazol-2-yl]methanesulfonamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)N=C(NS(=O)(=O)C(F)(F)F)S1 NQCZJQNFGCNRND-UHFFFAOYSA-N 0.000 claims 1
- VDBMNVXJMYNQQA-UHFFFAOYSA-N 1,1,1-trifluoro-n-[5-(4-methoxyphenyl)-4-phenyl-1,3-thiazol-2-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)N=C(NS(=O)(=O)C(F)(F)F)S1 VDBMNVXJMYNQQA-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 11
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 5
- 230000003266 anti-allergic effect Effects 0.000 abstract description 4
- 230000003424 uricosuric effect Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000002474 experimental method Methods 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 230000000144 pharmacologic effect Effects 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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- 235000010418 carrageenan Nutrition 0.000 description 10
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 210000002683 foot Anatomy 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XDWGEGZDMFHZBL-UHFFFAOYSA-N 4,5-diphenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XDWGEGZDMFHZBL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000700157 Rattus norvegicus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 208000009386 Experimental Arthritis Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
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- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CJUDGAVRXMGRLN-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 CJUDGAVRXMGRLN-UHFFFAOYSA-N 0.000 description 2
- VUQJYRXMLSGBKQ-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(N)=N1 VUQJYRXMLSGBKQ-UHFFFAOYSA-N 0.000 description 2
- KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 2
- KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
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- HCZKYJDFEPMADG-UHFFFAOYSA-N nordihydroguaiaretic acid Chemical compound C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- UTCMBAYRIVJABS-UHFFFAOYSA-N 1,1,1-trifluoro-n-[4-(4-methylphenyl)-5-phenyl-1,3-thiazol-2-yl]methanesulfonamide Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC=CC=2)SC(NS(=O)(=O)C(F)(F)F)=N1 UTCMBAYRIVJABS-UHFFFAOYSA-N 0.000 description 1
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- 230000037356 lipid metabolism Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- XDLMXYSENCWLQS-UHFFFAOYSA-N n-(4,5-diphenyl-1,3-thiazol-2-yl)methanesulfonamide Chemical compound S1C(NS(=O)(=O)C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XDLMXYSENCWLQS-UHFFFAOYSA-N 0.000 description 1
- BZBWTYGKYDLIOY-UHFFFAOYSA-N n-(furan-2-ylmethyl)-5-methyl-4-phenyl-1,3-thiazol-2-amine Chemical compound N=1C(C=2C=CC=CC=2)=C(C)SC=1NCC1=CC=CO1 BZBWTYGKYDLIOY-UHFFFAOYSA-N 0.000 description 1
- SJOZGRVSGZTULY-UHFFFAOYSA-N n-[4,5-bis(4-fluorophenyl)-1,3-thiazol-2-yl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)SC(NS(=O)(=O)C(F)(F)F)=N1 SJOZGRVSGZTULY-UHFFFAOYSA-N 0.000 description 1
- VRRXTQUHOCGGDR-UHFFFAOYSA-N n-[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(NS(=O)(=O)C(F)(F)F)=N1 VRRXTQUHOCGGDR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ouveaux dérivés diphénylthiazole dont la formule générale est la suivante (I) : (voir fig. I) (I) où m et n sont indépendamment 1 ou 2; R1 et R
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2105665 CA2105665C (fr) | 1991-03-07 | 1991-03-07 | Derives diphenylthiazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2105665 CA2105665C (fr) | 1991-03-07 | 1991-03-07 | Derives diphenylthiazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2105665A1 CA2105665A1 (fr) | 1992-09-08 |
| CA2105665C true CA2105665C (fr) | 1997-08-19 |
Family
ID=4152273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2105665 Expired - Fee Related CA2105665C (fr) | 1991-03-07 | 1991-03-07 | Derives diphenylthiazole |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2105665C (fr) |
-
1991
- 1991-03-07 CA CA 2105665 patent/CA2105665C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2105665A1 (fr) | 1992-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |