PT80833B - Process for preparing 2-benzyl-4-(4-pyridyl)thiazoles and derivatives thereof useful as immunoregulants - Google Patents
Process for preparing 2-benzyl-4-(4-pyridyl)thiazoles and derivatives thereof useful as immunoregulants Download PDFInfo
- Publication number
- PT80833B PT80833B PT80833A PT8083385A PT80833B PT 80833 B PT80833 B PT 80833B PT 80833 A PT80833 A PT 80833A PT 8083385 A PT8083385 A PT 8083385A PT 80833 B PT80833 B PT 80833B
- Authority
- PT
- Portugal
- Prior art keywords
- pyridyl
- thiazole
- benzyl
- alkyl
- hydrogen
- Prior art date
Links
- PZMNUBLMVHPYKL-UHFFFAOYSA-N 2-benzyl-4-pyridin-4-yl-1,3-thiazole Chemical class C=1C=CC=CC=1CC(SC=1)=NC=1C1=CC=NC=C1 PZMNUBLMVHPYKL-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- -1 1-Benzyl-4- (4-pyridyl) thiazole Chemical compound 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- MNJCKHLGQCHBRT-UHFFFAOYSA-N 2-[difluoro(phenyl)methyl]-4-pyridin-4-yl-1,3-thiazole Chemical compound C=1C=CC=CC=1C(F)(F)C(SC=1)=NC=1C1=CC=NC=C1 MNJCKHLGQCHBRT-UHFFFAOYSA-N 0.000 claims description 4
- KBPCLYRQLAMQLP-UHFFFAOYSA-N 2-benzyl-4-(2-chloropyridin-4-yl)-1,3-thiazole Chemical compound C1=NC(Cl)=CC(C=2N=C(CC=3C=CC=CC=3)SC=2)=C1 KBPCLYRQLAMQLP-UHFFFAOYSA-N 0.000 claims description 4
- JLSAFSPBUYUQCC-UHFFFAOYSA-N 2-phenyl-2-(4-pyridin-4-yl-1,3-thiazol-2-yl)acetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C(SC=1)=NC=1C1=CC=NC=C1 JLSAFSPBUYUQCC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- WYTOCODIWOEOOE-UHFFFAOYSA-N 2-[(4-nitrophenyl)methyl]-4-pyridin-4-yl-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=NC(C=2C=CN=CC=2)=CS1 WYTOCODIWOEOOE-UHFFFAOYSA-N 0.000 claims description 3
- NVZIVWOHNVWLTQ-UHFFFAOYSA-N 2-[(4-pyridin-4-yl-1,3-thiazol-2-yl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=NC(C=2C=CN=CC=2)=CS1 NVZIVWOHNVWLTQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- HUIQHXZGWOKGQM-UHFFFAOYSA-N 2-benzyl-4-(3-methoxypyridin-4-yl)-1,3-thiazole Chemical compound COC1=CN=CC=C1C1=CSC(CC=2C=CC=CC=2)=N1 HUIQHXZGWOKGQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- JPHRXLGOKFCSGI-UHFFFAOYSA-N n-[2-[(4-pyridin-4-yl-1,3-thiazol-2-yl)methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1CC1=NC(C=2C=CN=CC=2)=CS1 JPHRXLGOKFCSGI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- XDNZFKGBZKNWHX-UHFFFAOYSA-N 2-benzyl-4-(2-piperidin-1-ylpyridin-4-yl)-1,3-thiazole Chemical compound C=1C=CC=CC=1CC(SC=1)=NC=1C(C=1)=CC=NC=1N1CCCCC1 XDNZFKGBZKNWHX-UHFFFAOYSA-N 0.000 claims 1
- CAKKZLDLNWPXCI-UHFFFAOYSA-N 4-[4-(2-benzyl-1,3-thiazol-4-yl)pyridin-2-yl]morpholine Chemical compound C=1C=CC=CC=1CC(SC=1)=NC=1C(C=1)=CC=NC=1N1CCOCC1 CAKKZLDLNWPXCI-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- NAFCUKZZHZYPKB-UHFFFAOYSA-N 2-bromo-1-pyridin-4-ylethanone Chemical compound BrCC(=O)C1=CC=NC=C1 NAFCUKZZHZYPKB-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 0.000 abstract 1
- 150000003557 thiazoles Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
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- 239000003765 sweetening agent Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
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- 230000005764 inhibitory process Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- BCELSKZIQVOBEH-UHFFFAOYSA-N s-benzylthiohydroxylamine Chemical compound NSCC1=CC=CC=C1 BCELSKZIQVOBEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000003755 preservative agent Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- LAUFSGCBYZQRNG-UHFFFAOYSA-N 2,2-difluoro-2-phenylethanethioamide Chemical compound NC(=S)C(F)(F)C1=CC=CC=C1 LAUFSGCBYZQRNG-UHFFFAOYSA-N 0.000 description 3
- HZLJBAMWIBEFSZ-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-4-pyridin-4-yl-1,3-thiazole Chemical compound BrC1=CC=CC=C1CC1=NC(C=2C=CN=CC=2)=CS1 HZLJBAMWIBEFSZ-UHFFFAOYSA-N 0.000 description 3
- KJFZPJYARJJCRI-UHFFFAOYSA-N 2-benzyl-4-(1-oxidopyridin-1-ium-4-yl)-1,3-thiazole Chemical compound C1=C[N+]([O-])=CC=C1C1=CSC(CC=2C=CC=CC=2)=N1 KJFZPJYARJJCRI-UHFFFAOYSA-N 0.000 description 3
- TWQFKBIJNBKFMW-UHFFFAOYSA-N 2-chloro-4-pyridin-4-yl-1,3-thiazole Chemical compound S1C(Cl)=NC(C=2C=CN=CC=2)=C1 TWQFKBIJNBKFMW-UHFFFAOYSA-N 0.000 description 3
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
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- IMAQCQMTUQRZKA-UHFFFAOYSA-N phenyl-(4-pyridin-4-yl-1,3-thiazol-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C(SC=1)=NC=1C1=CC=NC=C1 IMAQCQMTUQRZKA-UHFFFAOYSA-N 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GQTWZLYQSMCSSU-UHFFFAOYSA-N 1-(3-methoxypyridin-4-yl)ethanone Chemical compound COC1=CN=CC=C1C(C)=O GQTWZLYQSMCSSU-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
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- FEMHZQZFCATIQC-UHFFFAOYSA-N 2-phenyl-2-(4-pyridin-4-yl-1,3-thiazol-2-yl)acetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)C(SC=1)=NC=1C1=CC=NC=C1 FEMHZQZFCATIQC-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- YOSOSDBZAUWJJT-UHFFFAOYSA-L sodium dithionite monohydrate Chemical compound O.[Na+].[Na+].[O-]S(=O)S([O-])=O YOSOSDBZAUWJJT-UHFFFAOYSA-L 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- VRKHAMWCGMJAMI-UHFFFAOYSA-M tetrahexylazanium;iodide Chemical compound [I-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC VRKHAMWCGMJAMI-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/634,094 US4697012A (en) | 1984-07-25 | 1984-07-25 | Morpholino pyridyl thiazole compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT80833A PT80833A (en) | 1985-08-01 |
| PT80833B true PT80833B (en) | 1987-05-27 |
Family
ID=24542414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT80833A PT80833B (en) | 1984-07-25 | 1985-07-18 | Process for preparing 2-benzyl-4-(4-pyridyl)thiazoles and derivatives thereof useful as immunoregulants |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4697012A (en]) |
| EP (1) | EP0169502B1 (en]) |
| JP (1) | JPS6137784A (en]) |
| KR (1) | KR860001105A (en]) |
| AU (1) | AU575666B2 (en]) |
| DE (1) | DE3580317D1 (en]) |
| DK (1) | DK336685A (en]) |
| ES (1) | ES8700255A1 (en]) |
| GR (1) | GR851809B (en]) |
| IL (1) | IL75823A0 (en]) |
| PT (1) | PT80833B (en]) |
| ZA (1) | ZA855581B (en]) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3486009T2 (de) * | 1983-09-09 | 1993-04-15 | Takeda Chemical Industries Ltd | 5-pyridyl-1,3-thiazol-derivate, ihre herstellung und anwendung. |
| GB9201692D0 (en) * | 1992-01-27 | 1992-03-11 | Smithkline Beecham Intercredit | Compounds |
| CN1065242C (zh) * | 1995-05-26 | 2001-05-02 | 拜尔公司 | 吡啶基－噻唑 |
| US7465736B2 (en) | 2002-06-14 | 2008-12-16 | Laboratoires Serono S.A. | Azole methylidene cyanide derivatives and their use as protein kinase modulators |
| AR045651A1 (es) * | 2003-09-19 | 2005-11-02 | Solvay Pharm Bv | Derivados de tiazol como moduladores del receptor de cannabinoide |
| US7294640B2 (en) | 2004-02-06 | 2007-11-13 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| AR083023A1 (es) * | 2010-09-17 | 2013-01-23 | Purdue Pharma Lp | Compuestos de piridina y una composicion farmaceutica que los comprende |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1112128A (en) * | 1965-12-22 | 1968-05-01 | Bellon Labor Sa Roger | New thiazolyl-diphenylmethane derivatives |
| IL28803A (en) * | 1966-11-18 | 1974-05-16 | Wyeth John & Brother Ltd | Oxazole and thiazole compounds,their preparation and pharmaceutical compositions containing them |
| CA962269A (en) * | 1971-05-05 | 1975-02-04 | Robert E. Grahame (Jr.) | Thiazoles, and their use as insecticides |
| US4153703A (en) * | 1977-06-30 | 1979-05-08 | Uniroyal, Inc. | Method of controlling insects and acarids with certain aryl-substituted thiazoles |
| DE3486009T2 (de) * | 1983-09-09 | 1993-04-15 | Takeda Chemical Industries Ltd | 5-pyridyl-1,3-thiazol-derivate, ihre herstellung und anwendung. |
-
1984
- 1984-07-25 US US06/634,094 patent/US4697012A/en not_active Expired - Fee Related
-
1985
- 1985-07-16 IL IL75823A patent/IL75823A0/xx unknown
- 1985-07-18 EP EP85108969A patent/EP0169502B1/en not_active Expired - Lifetime
- 1985-07-18 PT PT80833A patent/PT80833B/pt unknown
- 1985-07-18 DE DE8585108969T patent/DE3580317D1/de not_active Expired - Fee Related
- 1985-07-22 GR GR851809A patent/GR851809B/el unknown
- 1985-07-22 ES ES545439A patent/ES8700255A1/es not_active Expired
- 1985-07-24 AU AU45320/85A patent/AU575666B2/en not_active Expired - Fee Related
- 1985-07-24 DK DK336685A patent/DK336685A/da not_active Application Discontinuation
- 1985-07-24 ZA ZA855581A patent/ZA855581B/xx unknown
- 1985-07-24 KR KR1019850005279A patent/KR860001105A/ko not_active Ceased
- 1985-07-25 JP JP16308885A patent/JPS6137784A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES545439A0 (es) | 1986-10-01 |
| EP0169502B1 (en) | 1990-10-31 |
| AU575666B2 (en) | 1988-08-04 |
| PT80833A (en) | 1985-08-01 |
| US4697012A (en) | 1987-09-29 |
| IL75823A0 (en) | 1985-11-29 |
| DK336685A (da) | 1986-01-26 |
| EP0169502A2 (en) | 1986-01-29 |
| EP0169502A3 (en) | 1987-02-25 |
| ZA855581B (en) | 1986-03-26 |
| JPS6137784A (ja) | 1986-02-22 |
| DK336685D0 (da) | 1985-07-24 |
| DE3580317D1 (en) | 1990-12-13 |
| AU4532085A (en) | 1986-01-30 |
| GR851809B (en]) | 1985-11-26 |
| KR860001105A (ko) | 1986-02-22 |
| ES8700255A1 (es) | 1986-10-01 |
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