NO752752L - - Google Patents
Info
- Publication number
- NO752752L NO752752L NO752752A NO752752A NO752752L NO 752752 L NO752752 L NO 752752L NO 752752 A NO752752 A NO 752752A NO 752752 A NO752752 A NO 752752A NO 752752 L NO752752 L NO 752752L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- denotes
- diphenyloxazol
- thiol
- diphenyloxazole
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- -1 heterocyclic amino Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- ZOMUCVSKCXNYGL-UHFFFAOYSA-N (4,5-diphenyl-1,3-oxazol-2-yl)sulfanylformic acid Chemical class O1C(SC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZOMUCVSKCXNYGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ICEBUMPKMSKVHL-UHFFFAOYSA-N S-[(4,5-diphenyl-1,3-oxazol-2-yl)] carbamothioate Chemical class O1C(SC(=O)N)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ICEBUMPKMSKVHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
- STVVIBPFTMJJIZ-UHFFFAOYSA-N 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetic acid Chemical compound O1C(SCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 STVVIBPFTMJJIZ-UHFFFAOYSA-N 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical class CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical class CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- PAVIHTWMLRILFC-UHFFFAOYSA-N 2-chloro-4,5-diphenyl-1,3-oxazole Chemical compound O1C(Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PAVIHTWMLRILFC-UHFFFAOYSA-N 0.000 description 3
- NYQSTRUSYDZNHC-UHFFFAOYSA-N 4,5-diphenyl-3h-1,3-oxazole-2-thione Chemical compound O1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NYQSTRUSYDZNHC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 150000003573 thiols Chemical group 0.000 description 3
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 2
- HSUCJZWQZLSLMR-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-chloroacetate;hydrochloride Chemical compound Cl.ClCC(=O)OCCN1CCOCC1 HSUCJZWQZLSLMR-UHFFFAOYSA-N 0.000 description 2
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000004931 aggregating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- MDLNHSYXCATEOV-UHFFFAOYSA-N 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]propanoic acid Chemical compound O1C(SC(C)C(O)=O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MDLNHSYXCATEOV-UHFFFAOYSA-N 0.000 description 1
- SSXYKBHZZRYLLY-UHFFFAOYSA-N 2-chloro-1,3-oxazole Chemical compound ClC1=NC=CO1 SSXYKBHZZRYLLY-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- PWIGIOHIMSKJFG-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetate Chemical compound C1COCCN1CCOC(=O)CSC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWIGIOHIMSKJFG-UHFFFAOYSA-N 0.000 description 1
- RIRGCEBFARJZOH-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetate hydrochloride Chemical compound Cl.C1COCCN1CCOC(=O)CSC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RIRGCEBFARJZOH-UHFFFAOYSA-N 0.000 description 1
- GYXHHICIFZSKKZ-UHFFFAOYSA-N 2-sulfanylacetamide Chemical compound NC(=O)CS GYXHHICIFZSKKZ-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- DFNQSOKTVWZOJK-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetamide Chemical compound CN(CCNC(CSC=1OC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1)=O)C DFNQSOKTVWZOJK-UHFFFAOYSA-N 0.000 description 1
- ZNPJTSPFQAJKHW-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetamide hydrochloride Chemical compound Cl.CN(CCNC(CSC=1OC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1)=O)C ZNPJTSPFQAJKHW-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108091006503 SLC26A1 Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LPFNYZLGCZCARW-UHFFFAOYSA-N ethyl 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]acetate Chemical compound O1C(SCC(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LPFNYZLGCZCARW-UHFFFAOYSA-N 0.000 description 1
- VYGYKYFGCVRZGN-UHFFFAOYSA-N ethyl 2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]propanoate Chemical compound O1C(SC(C)C(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VYGYKYFGCVRZGN-UHFFFAOYSA-N 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/46—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34673/74A GB1507032A (en) | 1974-08-06 | 1974-08-06 | 2-thiol-4,5-diphenyloxazole s-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO752752L true NO752752L (xx) | 1976-02-09 |
Family
ID=10368553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO752752A NO752752L (xx) | 1974-08-06 | 1975-08-05 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4001228A (xx) |
| JP (1) | JPS5143756A (xx) |
| AR (1) | AR205653A1 (xx) |
| AT (1) | AT348518B (xx) |
| BE (1) | BE832188A (xx) |
| CA (1) | CA1036599A (xx) |
| CH (1) | CH621780A5 (xx) |
| DE (1) | DE2535147A1 (xx) |
| DK (1) | DK356375A (xx) |
| ES (1) | ES439909A1 (xx) |
| FR (1) | FR2281115A1 (xx) |
| GB (1) | GB1507032A (xx) |
| IL (1) | IL47878A (xx) |
| NL (1) | NL7509013A (xx) |
| NO (1) | NO752752L (xx) |
| SE (1) | SE7508724L (xx) |
| ZA (1) | ZA754630B (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1099996B (it) * | 1978-10-17 | 1985-09-28 | Anic Spa | Derivati del 4,5-difenil-ossazolo 2-ammino o 2-tio sostituiti e procedimento per il loro ottenimento |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| IL90192A0 (en) * | 1988-05-13 | 1989-12-15 | Schering Ag | Azole ether derivatives and pesticidal compositions containing the same |
| NZ236474A (en) * | 1989-12-20 | 1993-07-27 | Bristol Myers Squibb Co | 4,5-diphenyl-2-oxazole octanoic, nonanoic and decanoic acid and ester derivatives, preparation and pharmaceutical compositions thereof |
| US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
| FR2753449B1 (fr) * | 1996-09-13 | 1998-12-04 | Union Pharma Scient Appl | Nouveaux derives 3,4-diaryloxazolone, leurs procedes de preparation, et leurs utilisations en therapeutique |
| US7358254B2 (en) * | 2001-07-13 | 2008-04-15 | Bristol-Myers Squibb Company | Method for treating atherosclerosis employing an aP2 inhibitor and combination |
| PL346660A1 (en) | 1998-09-17 | 2002-02-25 | Bristol Myers Squibb Co | Method for treating atherosclerosis employing an ap2 inhibitor and combination |
| US7390824B1 (en) | 1999-09-07 | 2008-06-24 | Bristol-Myers Squibb Company | Method for treating diabetes employing an aP2 inhibitor and combination |
| WO2023143741A1 (de) * | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2129012A1 (de) * | 1971-06-11 | 1973-01-04 | Merck Patent Gmbh | Azol-derivate |
| FR2156486A1 (en) * | 1971-10-22 | 1973-06-01 | Roussel Uclaf | Oxazolyl oxy or thio acetic acids - analgesics antipyretics and anti-inflammatories |
-
1974
- 1974-08-06 GB GB34673/74A patent/GB1507032A/en not_active Expired
-
1975
- 1975-01-01 AR AR259879A patent/AR205653A1/es active
- 1975-07-18 ZA ZA00754630A patent/ZA754630B/xx unknown
- 1975-07-23 US US05/598,186 patent/US4001228A/en not_active Expired - Lifetime
- 1975-07-24 AT AT575475A patent/AT348518B/de not_active IP Right Cessation
- 1975-07-29 NL NL7509013A patent/NL7509013A/xx not_active Application Discontinuation
- 1975-07-29 CA CA232,493A patent/CA1036599A/en not_active Expired
- 1975-07-31 ES ES439909A patent/ES439909A1/es not_active Expired
- 1975-08-01 SE SE7508724A patent/SE7508724L/xx unknown
- 1975-08-05 IL IL7547878A patent/IL47878A/xx unknown
- 1975-08-05 NO NO752752A patent/NO752752L/no unknown
- 1975-08-05 FR FR7524383A patent/FR2281115A1/fr active Granted
- 1975-08-05 CH CH1019375A patent/CH621780A5/de not_active IP Right Cessation
- 1975-08-05 DK DK356375A patent/DK356375A/da unknown
- 1975-08-06 BE BE158995A patent/BE832188A/xx not_active IP Right Cessation
- 1975-08-06 DE DE19752535147 patent/DE2535147A1/de not_active Ceased
- 1975-08-06 JP JP50095094A patent/JPS5143756A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA754630B (en) | 1976-07-28 |
| IL47878A (en) | 1979-01-31 |
| NL7509013A (nl) | 1976-02-10 |
| DE2535147A1 (de) | 1976-02-19 |
| AT348518B (de) | 1979-02-26 |
| IL47878A0 (en) | 1975-11-25 |
| AU8367075A (en) | 1977-02-10 |
| DK356375A (da) | 1976-02-07 |
| FR2281115B1 (xx) | 1978-11-10 |
| ES439909A1 (es) | 1977-08-16 |
| BE832188A (fr) | 1975-12-01 |
| SE7508724L (sv) | 1976-02-09 |
| ATA575475A (de) | 1978-07-15 |
| FR2281115A1 (fr) | 1976-03-05 |
| US4001228A (en) | 1977-01-04 |
| GB1507032A (en) | 1978-04-12 |
| CH621780A5 (xx) | 1981-02-27 |
| AR205653A1 (es) | 1976-05-21 |
| JPS5143756A (en) | 1976-04-14 |
| CA1036599A (en) | 1978-08-15 |
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