NO325518B1 - Nye fettsyrederivater - Google Patents
Nye fettsyrederivater Download PDFInfo
- Publication number
- NO325518B1 NO325518B1 NO19993563A NO993563A NO325518B1 NO 325518 B1 NO325518 B1 NO 325518B1 NO 19993563 A NO19993563 A NO 19993563A NO 993563 A NO993563 A NO 993563A NO 325518 B1 NO325518 B1 NO 325518B1
- Authority
- NO
- Norway
- Prior art keywords
- lipophilic
- acid
- compound
- cis
- derivative according
- Prior art date
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- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 239000003814 drug Substances 0.000 claims abstract description 100
- 229940079593 drug Drugs 0.000 claims abstract description 98
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 95
- -1 trans-8-heptadecenyl Chemical group 0.000 claims abstract description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000000524 functional group Chemical group 0.000 claims abstract description 35
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 14
- 239000003905 agrochemical Substances 0.000 claims abstract description 8
- 150000003573 thiols Chemical class 0.000 claims abstract description 8
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 38
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 34
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 34
- 150000001408 amides Chemical class 0.000 claims description 34
- 229960002009 naproxen Drugs 0.000 claims description 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 26
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 19
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 19
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 18
- 229960005205 prednisolone Drugs 0.000 claims description 17
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 16
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 16
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 15
- 229960004679 doxorubicin Drugs 0.000 claims description 15
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 15
- 229960004630 chlorambucil Drugs 0.000 claims description 13
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 12
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 12
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 12
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 11
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 11
- 229960000975 daunorubicin Drugs 0.000 claims description 11
- 229960001924 melphalan Drugs 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 10
- 229960000723 ampicillin Drugs 0.000 claims description 10
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 10
- 229960002702 piroxicam Drugs 0.000 claims description 10
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 10
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 9
- 229960002537 betamethasone Drugs 0.000 claims description 8
- 229960001259 diclofenac Drugs 0.000 claims description 8
- 239000002327 cardiovascular agent Substances 0.000 claims description 7
- 229940125692 cardiovascular agent Drugs 0.000 claims description 7
- 229960004171 hydroxychloroquine Drugs 0.000 claims description 7
- 229960004889 salicylic acid Drugs 0.000 claims description 7
- 239000003470 adrenal cortex hormone Substances 0.000 claims description 6
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 6
- 239000004599 antimicrobial Substances 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 6
- YGULWPYYGQCFMP-CEAXSRTFSA-N Metoprolol tartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 YGULWPYYGQCFMP-CEAXSRTFSA-N 0.000 claims description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims description 5
- 239000003096 antiparasitic agent Substances 0.000 claims description 5
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 4
- 229930012538 Paclitaxel Natural products 0.000 claims description 4
- UUBUNFOPMSFGBM-KTKRTIGZSA-N [(z)-octadec-9-enyl] carbamate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(N)=O UUBUNFOPMSFGBM-KTKRTIGZSA-N 0.000 claims description 4
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 4
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 4
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 229960000905 indomethacin Drugs 0.000 claims description 4
- 229960001019 oxacillin Drugs 0.000 claims description 4
- 229960001592 paclitaxel Drugs 0.000 claims description 4
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 3
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 3
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 3
- 229960005091 chloramphenicol Drugs 0.000 claims description 3
- 229960004397 cyclophosphamide Drugs 0.000 claims description 3
- 229960000901 mepacrine Drugs 0.000 claims description 3
- 229960000485 methotrexate Drugs 0.000 claims description 3
- GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 claims description 3
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims description 2
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 claims description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
- XILVEPYQJIOVNB-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester Chemical compound OCCOCCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 XILVEPYQJIOVNB-UHFFFAOYSA-N 0.000 claims description 2
- JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 claims description 2
- GXEUNRBWEAIPCN-UHFFFAOYSA-N 2-chloro-2-(3-chloro-4-cyclohexylphenyl)acetic acid Chemical compound ClC1=CC(C(Cl)C(=O)O)=CC=C1C1CCCCC1 GXEUNRBWEAIPCN-UHFFFAOYSA-N 0.000 claims description 2
- FJYDZDFPRKABNP-MDZDMXLPSA-N 2-hydroxy-4-[[(e)-octadec-9-enoyl]amino]benzoic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)NC1=CC=C(C(O)=O)C(O)=C1 FJYDZDFPRKABNP-MDZDMXLPSA-N 0.000 claims description 2
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims description 2
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 claims description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 2
- PBBGSZCBWVPOOL-HDICACEKSA-N 4-[(1r,2s)-1-ethyl-2-(4-hydroxyphenyl)butyl]phenol Chemical compound C1([C@H](CC)[C@H](CC)C=2C=CC(O)=CC=2)=CC=C(O)C=C1 PBBGSZCBWVPOOL-HDICACEKSA-N 0.000 claims description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 2
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000005489 Bromoxynil Substances 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 claims description 2
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
- QMLVECGLEOSESV-RYUDHWBXSA-N Danofloxacin Chemical compound C([C@@H]1C[C@H]2CN1C)N2C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1CC1 QMLVECGLEOSESV-RYUDHWBXSA-N 0.000 claims description 2
- ZEFNOZRLAWVAQF-UHFFFAOYSA-N Dinitolmide Chemical compound CC1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZEFNOZRLAWVAQF-UHFFFAOYSA-N 0.000 claims description 2
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 claims description 2
- 108010061435 Enalapril Proteins 0.000 claims description 2
- OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 2
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 2
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 claims description 2
- MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 claims description 2
- 239000005595 Picloram Substances 0.000 claims description 2
- KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 claims description 2
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 claims description 2
- 229960004892 acemetacin Drugs 0.000 claims description 2
- FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 claims description 2
- 229960005142 alclofenac Drugs 0.000 claims description 2
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB9701441A GB2321455A (en) | 1997-01-24 | 1997-01-24 | Lipophilic derivatives of biologically active compounds |
PCT/NO1998/000021 WO1998032718A1 (en) | 1997-01-24 | 1998-01-23 | New fatty acid derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO993563D0 NO993563D0 (no) | 1999-07-21 |
NO993563L NO993563L (no) | 1999-09-17 |
NO325518B1 true NO325518B1 (no) | 2008-06-02 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19993563A NO325518B1 (no) | 1997-01-24 | 1999-07-21 | Nye fettsyrederivater |
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US (3) | US20010006962A1 (sk) |
EP (1) | EP0977725B1 (sk) |
JP (2) | JP4698773B2 (sk) |
KR (1) | KR100546457B1 (sk) |
AT (1) | ATE269292T1 (sk) |
AU (1) | AU733370B2 (sk) |
CA (1) | CA2276694C (sk) |
CZ (1) | CZ299815B6 (sk) |
DE (1) | DE69824574T2 (sk) |
DK (1) | DK0977725T3 (sk) |
ES (1) | ES2224356T3 (sk) |
GB (1) | GB2321455A (sk) |
HU (1) | HU225664B1 (sk) |
IL (1) | IL130853A (sk) |
NO (1) | NO325518B1 (sk) |
NZ (1) | NZ336724A (sk) |
PL (1) | PL196831B1 (sk) |
RU (1) | RU2227794C2 (sk) |
SK (1) | SK284803B6 (sk) |
TW (1) | TWI231209B (sk) |
UA (1) | UA65557C2 (sk) |
WO (1) | WO1998032718A1 (sk) |
ZA (1) | ZA98579B (sk) |
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US6207700B1 (en) * | 1999-01-07 | 2001-03-27 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
US7235583B1 (en) * | 1999-03-09 | 2007-06-26 | Luitpold Pharmaceuticals, Inc., | Fatty acid-anticancer conjugates and uses thereof |
AU2002303164A1 (en) | 2001-03-23 | 2002-10-08 | Protarga, Inc. | Fatty amine drug conjugates |
WO2002076404A2 (en) * | 2001-03-23 | 2002-10-03 | Protarga, Inc. | Fatty alcohol drug conjugates |
BR0312584A (pt) * | 2002-07-08 | 2005-04-12 | Pliva Istrazivacki Inst D O O | Novas substâncias anti-inflamatórias não-esteróides, compostos e métodos para o uso das mesmas |
JP4530851B2 (ja) * | 2002-07-08 | 2010-08-25 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | ステロイド/非ステロイド抗炎症活性分子、抗新生物活性分子および抗ウイルス活性分子用担体としての新規な化合物、組成物 |
CN100577681C (zh) * | 2002-07-08 | 2010-01-06 | 葛兰素伊斯特拉齐瓦基森塔萨格勒布公司 | 用于治疗炎性疾病和病症的新化合物、组合物和方法 |
US20040235811A1 (en) | 2002-10-08 | 2004-11-25 | Sepracor Inc. | Fatty acid modified forms of glucocorticoids |
US7196082B2 (en) * | 2002-11-08 | 2007-03-27 | Merck & Co. Inc. | Ophthalmic compositions for treating ocular hypertension |
GB0304927D0 (en) | 2003-03-04 | 2003-04-09 | Resolution Chemicals Ltd | Process for the production of tibolone |
CA2562783A1 (en) | 2004-04-26 | 2005-12-01 | Vanderbilt University | Indoleacetic acid and indenacetic acid derivatives as therapeutic agents with reduced gastrointestinal toxicity |
NO324263B1 (no) | 2005-12-08 | 2007-09-17 | Clavis Pharma Asa | Kjemiske forbindelser, anvendelse derav ved behandling av kreft, samt farmasoytiske preparater som omfatter slike forbindelser |
US8497292B2 (en) * | 2005-12-28 | 2013-07-30 | Translational Therapeutics, Inc. | Translational dysfunction based therapeutics |
WO2007149456A2 (en) | 2006-06-19 | 2007-12-27 | Vanderbilt University | Methods and compositions for diagnostic and therapeutic targeting of cox-2 |
NO331891B1 (no) * | 2007-03-20 | 2012-04-30 | Clavis Pharma Asa | Kjemiske forbindelser, et farmasoytisk preparat inneholdende slike forbindelser, samt anvendelse derav for behandling av kreft, inflammasjon og KOLS |
EP2205073A4 (en) * | 2007-09-26 | 2013-03-06 | Sinai School Medicine | AZACYTIDINE ANALOGS AND USES THEREOF |
WO2010028458A1 (en) * | 2008-09-12 | 2010-03-18 | Parnell Laboratories (Aust) Pty Ltd | Prodrugs of isoxazolyl penicillins and uses thereof |
JP5805086B2 (ja) * | 2009-08-26 | 2015-11-04 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 抗微生物性アミノサリチル酸誘導体 |
WO2012174121A2 (en) * | 2011-06-13 | 2012-12-20 | The University Of Kansas | Decoquinate prodrugs |
EP2768499A4 (en) | 2011-10-17 | 2015-08-26 | Univ Vanderbilt | INDOMETACIN ANALOGUES FOR THE TREATMENT OF CANCER PROSTATE RESISTANT TO CASTRATION |
WO2013161993A1 (ja) | 2012-04-27 | 2013-10-31 | 日本臓器製薬株式会社 | トランス-2-デセン酸誘導体及びこれを含有する医薬 |
CN103450141B (zh) * | 2013-08-23 | 2015-08-26 | 山东鲁抗舍里乐药业有限公司 | 一种苯并吡喃酮类化合物、其制备方法及其应用 |
WO2018191789A1 (en) | 2017-04-21 | 2018-10-25 | University Of Tasmania | Therapeutic compounds and methods |
CN111116374B (zh) * | 2019-12-04 | 2020-12-15 | 北京理工大学 | 一种氨鲁米特与2-硝基苯甲酸合成π-π键共晶体的方法 |
JP7231576B2 (ja) | 2020-03-09 | 2023-03-01 | 株式会社日立ハイテク | 電解質濃度測定装置 |
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FR2485001A1 (fr) * | 1980-06-02 | 1981-12-24 | Svatos Antonin | Esters de l'acide ricinoleique et de chloroxylenols et compositions antiparasitaires |
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US4554279A (en) * | 1981-01-29 | 1985-11-19 | The United States Of America As Represented By The Secretary Of The Army | 5-(Straight chain 3-12 carbon alkoxy)-8-quinolinamines and their use for treatment of malaria |
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DE3625738A1 (de) * | 1986-07-30 | 1988-02-11 | Goedecke Ag | 2-acyloxypropylamin-derivate, verfahren zu deren herstellung und deren verwendung |
DE3887544T2 (de) * | 1987-03-09 | 1994-06-01 | Procter & Gamble | Beta-aminoethyl-substituierte Phenyl-Verbindungen, diese enthaltende entzündungshemmende oder analgetische Zusammensetzungen. |
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-
1997
- 1997-01-24 GB GB9701441A patent/GB2321455A/en not_active Withdrawn
-
1998
- 1998-01-23 AT AT98901593T patent/ATE269292T1/de active
- 1998-01-23 JP JP53186398A patent/JP4698773B2/ja not_active Expired - Lifetime
- 1998-01-23 RU RU99118313/04A patent/RU2227794C2/ru not_active IP Right Cessation
- 1998-01-23 AU AU57828/98A patent/AU733370B2/en not_active Expired
- 1998-01-23 ZA ZA98579A patent/ZA98579B/xx unknown
- 1998-01-23 EP EP98901593A patent/EP0977725B1/en not_active Expired - Lifetime
- 1998-01-23 SK SK1003-99A patent/SK284803B6/sk not_active IP Right Cessation
- 1998-01-23 WO PCT/NO1998/000021 patent/WO1998032718A1/en active IP Right Grant
- 1998-01-23 HU HU0000937A patent/HU225664B1/hu not_active IP Right Cessation
- 1998-01-23 ES ES98901593T patent/ES2224356T3/es not_active Expired - Lifetime
- 1998-01-23 CZ CZ0247799A patent/CZ299815B6/cs not_active IP Right Cessation
- 1998-01-23 NZ NZ336724A patent/NZ336724A/en not_active IP Right Cessation
- 1998-01-23 PL PL334919A patent/PL196831B1/pl unknown
- 1998-01-23 IL IL13085398A patent/IL130853A/xx not_active IP Right Cessation
- 1998-01-23 US US09/355,111 patent/US20010006962A1/en not_active Abandoned
- 1998-01-23 DE DE69824574T patent/DE69824574T2/de not_active Expired - Lifetime
- 1998-01-23 DK DK98901593T patent/DK0977725T3/da active
- 1998-01-23 UA UA99084762A patent/UA65557C2/uk unknown
- 1998-01-23 CA CA002276694A patent/CA2276694C/en not_active Expired - Lifetime
- 1998-01-23 KR KR1019997006548A patent/KR100546457B1/ko not_active IP Right Cessation
- 1998-03-13 TW TW087103693A patent/TWI231209B/zh not_active IP Right Cessation
-
1999
- 1999-07-21 NO NO19993563A patent/NO325518B1/no not_active IP Right Cessation
-
2002
- 2002-04-05 US US10/116,358 patent/US6762175B2/en not_active Expired - Lifetime
-
2003
- 2003-09-16 US US10/662,441 patent/US20040063677A1/en not_active Abandoned
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2009
- 2009-06-12 JP JP2009141714A patent/JP5232083B2/ja not_active Expired - Lifetime
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