CA1127084A - Imidazothiazole anti-inflammatoire - Google Patents

Imidazothiazole anti-inflammatoire

Info

Publication number: CA1127084A
Authority: CA; Canada
Prior art keywords: phenyl; hydrogen; compound; preparation; methyl
Prior art date: 1976-01-19
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

Application number

CA364,188A

Other languages

English (en)

Inventor

Robert E. Moser

Larry J. Powers

Zaven S. Ariyan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Diamond Shamrock Corp

Original Assignee

Diamond Shamrock Corp

Priority date (The priority date 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 date listed.)

1976-01-19

Filing date

1980-11-06

Publication date

1982-07-06

1976-01-19 Priority claimed from US05/650,318 external-priority patent/US4041167A/en

1977-01-18 Priority claimed from CA269,924A external-priority patent/CA1095524A/fr

1980-11-06 Application filed by Diamond Shamrock Corp filed Critical Diamond Shamrock Corp

1980-11-06 Priority to CA364,188A priority Critical patent/CA1127084A/fr

1982-07-06 Application granted granted Critical

1982-07-06 Publication of CA1127084A publication Critical patent/CA1127084A/fr

Status Expired legal-status Critical Current

Links

230000003110 anti-inflammatory effect Effects 0.000 title claims description 16
UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical class C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 60
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
-1 2-benzofuranyl Chemical group 0.000 claims abstract description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
150000003839 salts Chemical group 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 9
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims description 14
239000004480 active ingredient Substances 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
125000004799 bromophenyl group Chemical group 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
238000007911 parenteral administration Methods 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
IQTAGLNYWZMGGX-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC=C2OC(C3=CSC=4N3CCN=4)=CC2=C1 IQTAGLNYWZMGGX-UHFFFAOYSA-N 0.000 claims 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 14
241001465754 Metazoa Species 0.000 abstract description 10
239000002243 precursor Substances 0.000 abstract description 5
206010018691 Granuloma Diseases 0.000 abstract description 4
150000008634 thiazolopyrimidines Chemical class 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000000034 method Methods 0.000 description 15
239000000203 mixture Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
238000010992 reflux Methods 0.000 description 10
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
210000002683 foot Anatomy 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
150000003557 thiazoles Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
206010030113 Oedema Diseases 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
235000010418 carrageenan Nutrition 0.000 description 5
229920001525 carrageenan Polymers 0.000 description 5
210000000548 hind-foot Anatomy 0.000 description 5
239000007787 solid Substances 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
FOOHWUQIWMQCQA-UHFFFAOYSA-N n-phenyl-1,3-thiazole-2-carboxamide Chemical compound N=1C=CSC=1C(=O)NC1=CC=CC=C1 FOOHWUQIWMQCQA-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
230000003902 lesion Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WXASPCLYKBMWTE-UHFFFAOYSA-N Cl.N=1C=CSC=1C(=O)NC1=CC=CC=C1 Chemical compound Cl.N=1C=CSC=1C(=O)NC1=CC=CC=C1 WXASPCLYKBMWTE-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical group OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
229940093499 ethyl acetate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
150000003230 pyrimidines Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
HEPOCOLSLPZREJ-UHFFFAOYSA-N 3-methyl-n-(2,4,6-trimethylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole-2-carboxamide Chemical compound S1C2=NCCN2C(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C HEPOCOLSLPZREJ-UHFFFAOYSA-N 0.000 description 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
JLETUFGLJXMETA-UHFFFAOYSA-N 6-(4-nitrophenyl)imidazo[2,1-b][1,3]thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN(C=CS2)C2=N1 JLETUFGLJXMETA-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000182988 Assa Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
101150039033 Eci2 gene Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
RDPDIFVNASWMNH-UHFFFAOYSA-N O1C(=CC2=C1C=CC=C2)C(Br)C(=O)C(C=1OC2=C(C=1)C=CC=C2)Br Chemical compound O1C(=CC2=C1C=CC=C2)C(Br)C(=O)C(C=1OC2=C(C=1)C=CC=C2)Br RDPDIFVNASWMNH-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000534944 Thia Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000001780 adrenocortical effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
229940124599 anti-inflammatory drug Drugs 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
125000006286 dichlorobenzyl group Chemical group 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229940126904 hypoglycaemic agent Drugs 0.000 description 1
APWIQNJBGHKQRN-UHFFFAOYSA-N imidazolidine-2-thiol Chemical compound SC1NCCN1 APWIQNJBGHKQRN-UHFFFAOYSA-N 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical group C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
125000005289 uranyl group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA364,188A 1976-01-19 1980-11-06 Imidazothiazole anti-inflammatoire Expired CA1127084A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA364,188A CA1127084A (fr)	1976-01-19	1980-11-06	Imidazothiazole anti-inflammatoire

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US05/650,318 US4041167A (en)	1976-01-19	1976-01-19	Antiinflammatory imidazothiazoles
US650,318		1976-01-19
US05/753,350 US4103016A (en)	1976-01-19	1976-12-22	Antiinflammatory imidazothiazoles and thiazolopyrimidines
US753,350		1976-12-23
CA269,924A CA1095524A (fr)	1976-01-19	1977-01-18	Imidazothiazoles employes comme anti-inflammatoires
CA364,188A CA1127084A (fr)	1976-01-19	1980-11-06	Imidazothiazole anti-inflammatoire

Publications (1)

Publication Number	Publication Date
CA1127084A true CA1127084A (fr)	1982-07-06

Family

ID=27425970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA364,188A Expired CA1127084A (fr)	1976-01-19	1980-11-06	Imidazothiazole anti-inflammatoire

Country Status (1)

Country	Link
CA (1)	CA1127084A (fr)

1980
- 1980-11-06 CA CA364,188A patent/CA1127084A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-07-06	MKEX	Expiry

Publication	Publication Date	Title
JP3199451B2 (ja)	2001-08-20	２−アシルアミノ−５−チアゾール誘導体、製法および組成物
US4233299A (en)	1980-11-11	4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides and salts thereof
US4186200A (en)	1980-01-29	Novel fused derivatives of 2-pyridones
FI93012B (fi)	1994-10-31	Menetelmä terapeuttisesti käyttökelpoisten (1-hydroksi-2-piperidinoalkyyli)-2-indoloni-, 2-kinoloni-, 2-bentso/b/-atsepinoni-, bentsimidatsoloni- ja 2-kinatsolinonijohdannaisten valmistamiseksi
WO2004098494A2 (fr)	2004-11-18	Composés, compositions et procédés
HU201553B (en)	1990-11-28	Process for producing tetrahydrofuro- and -thieno(2,3-c)pyridines and pharmaceutical compositions comprising same
Ogawva et al.	1993	Syntheses of substituted 2, 4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors
US4110460A (en)	1978-08-29	2,3-Dihydro-imidazo[2,1-b]-thiazole derivatives and applications thereof
US3455924A (en)	1969-07-15	Dianisylimidazoles
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