JPH0354666B2 - - Google Patents
Info
- Publication number
- JPH0354666B2 JPH0354666B2 JP57196248A JP19624882A JPH0354666B2 JP H0354666 B2 JPH0354666 B2 JP H0354666B2 JP 57196248 A JP57196248 A JP 57196248A JP 19624882 A JP19624882 A JP 19624882A JP H0354666 B2 JPH0354666 B2 JP H0354666B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acid residue
- residue
- formula
- above formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 31
- -1 terpene acids Chemical class 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 14
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 5
- 235000007586 terpenes Nutrition 0.000 claims description 5
- WJHFZYAELPOJIV-IJFRVEDASA-N (2E,6E)-farnesoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C(O)=O WJHFZYAELPOJIV-IJFRVEDASA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005472 straight-chain saturated fatty acid group Chemical group 0.000 claims description 4
- 150000003505 terpenes Chemical class 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 229930002330 retinoic acid Natural products 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- AKVBCGQVQXPRLD-UHFFFAOYSA-N 2-aminooctanoic acid Chemical group CCCCCCC(N)C(O)=O AKVBCGQVQXPRLD-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- WJUCVNVYISECTJ-BQYQJAHWSA-N (e)-3-methyloct-2-enoic acid Chemical group CCCCC\C(C)=C\C(O)=O WJUCVNVYISECTJ-BQYQJAHWSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000008342 Leukemia P388 Diseases 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 3
- NTWSIWWJPQHFTO-AATRIKPKSA-N (2E)-3-methylhex-2-enoic acid Chemical group CCC\C(C)=C\C(O)=O NTWSIWWJPQHFTO-AATRIKPKSA-N 0.000 description 2
- AKVBCGQVQXPRLD-SSDOTTSWSA-N (2r)-2-azaniumyloctanoate Chemical group CCCCCC[C@@H]([NH3+])C([O-])=O AKVBCGQVQXPRLD-SSDOTTSWSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical group CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- AKVBCGQVQXPRLD-ZETCQYMHSA-N (2s)-2-azaniumyloctanoate Chemical group CCCCCC[C@H]([NH3+])C([O-])=O AKVBCGQVQXPRLD-ZETCQYMHSA-N 0.000 description 2
- GVKGXDFZFAFBIW-MQQKCMAXSA-N (4e,6e)-octa-4,6-dienoic acid Chemical group C\C=C\C=C\CCC(O)=O GVKGXDFZFAFBIW-MQQKCMAXSA-N 0.000 description 2
- BLROLNSSBGCUAD-GQCTYLIASA-N (e)-3,4-dimethylpent-2-enoic acid Chemical group CC(C)C(\C)=C\C(O)=O BLROLNSSBGCUAD-GQCTYLIASA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- JZXHUPALAOUFMA-UHFFFAOYSA-N 2-amino-tridecanoic acid Chemical group CCCCCCCCCCCC(N)C(O)=O JZXHUPALAOUFMA-UHFFFAOYSA-N 0.000 description 2
- QUBNFZFTFXTLKH-UHFFFAOYSA-N 2-aminododecanoic acid Chemical group CCCCCCCCCCC(N)C(O)=O QUBNFZFTFXTLKH-UHFFFAOYSA-N 0.000 description 2
- RDFMDVXONNIGBC-UHFFFAOYSA-N 2-aminoheptanoic acid Chemical group CCCCCC(N)C(O)=O RDFMDVXONNIGBC-UHFFFAOYSA-N 0.000 description 2
- XRKBQVGBWJWJJJ-UHFFFAOYSA-N 2-aminooctadecanoic acid Chemical group CCCCCCCCCCCCCCCCC(N)C(O)=O XRKBQVGBWJWJJJ-UHFFFAOYSA-N 0.000 description 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical group CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 2
- KWNGIKVZXFFZNN-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1Cl.CC1=CC=C(S([O-])(=O)=O)C=C1 KWNGIKVZXFFZNN-UHFFFAOYSA-M 0.000 description 2
- HQWDKLAIDBOLFE-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1F.CC1=CC=C(S([O-])(=O)=O)C=C1 HQWDKLAIDBOLFE-UHFFFAOYSA-M 0.000 description 2
- JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical group CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 2
- BTJFTHOOADNOOS-UHFFFAOYSA-N 2-hydroxynonanoic acid Chemical group CCCCCCCC(O)C(O)=O BTJFTHOOADNOOS-UHFFFAOYSA-N 0.000 description 2
- FSHGKCLIZVPYIQ-UHFFFAOYSA-N 2-undecynoic acid Chemical group CCCCCCCCC#CC(O)=O FSHGKCLIZVPYIQ-UHFFFAOYSA-N 0.000 description 2
- VJIPBFNHEUXWKB-UHFFFAOYSA-N 3,4-dimethylhept-2-enoic acid Chemical group CCCC(C)C(C)=CC(O)=O VJIPBFNHEUXWKB-UHFFFAOYSA-N 0.000 description 2
- OWEJJGZFCSZDII-UHFFFAOYSA-N 3,4-dimethyltetradec-2-enoic acid Chemical group CCCCCCCCCCC(C)C(C)=CC(O)=O OWEJJGZFCSZDII-UHFFFAOYSA-N 0.000 description 2
- KWQCCGWSFMZMBP-UHFFFAOYSA-N 3,4-dimethylundec-2-enoic acid Chemical group CCCCCCCC(C)C(C)=CC(O)=O KWQCCGWSFMZMBP-UHFFFAOYSA-N 0.000 description 2
- YKUOQEJKIPNUEA-UHFFFAOYSA-N 3-methyldodec-2-enoic acid Chemical group CCCCCCCCCC(C)=CC(O)=O YKUOQEJKIPNUEA-UHFFFAOYSA-N 0.000 description 2
- AGRVEAUDGQSNMX-UHFFFAOYSA-N 3-methyltetradec-2-enoic acid Chemical group CCCCCCCCCCCC(C)=CC(O)=O AGRVEAUDGQSNMX-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical group NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical group CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical group CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical group NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- VHVMWCWIYITOLN-UHFFFAOYSA-N heptadec-2-ynoic acid Chemical group CCCCCCCCCCCCCCC#CC(O)=O VHVMWCWIYITOLN-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical group CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical group CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- GEHPRJRWZDWFBJ-FOCLMDBBSA-N (2E)-2-heptadecenoic acid Chemical group CCCCCCCCCCCCCC\C=C\C(O)=O GEHPRJRWZDWFBJ-FOCLMDBBSA-N 0.000 description 1
- CRJWOABTAHMMSA-MRXNPFEDSA-N (2R)-2-aminoheptadecanoic acid Chemical group CCCCCCCCCCCCCCC[C@@H](N)C(O)=O CRJWOABTAHMMSA-MRXNPFEDSA-N 0.000 description 1
- XRKBQVGBWJWJJJ-QGZVFWFLSA-N (2R)-2-aminooctadecanoic acid Chemical group CCCCCCCCCCCCCCCC[C@@H](N)C(O)=O XRKBQVGBWJWJJJ-QGZVFWFLSA-N 0.000 description 1
- XEDDSVXNGSVIKY-CQSZACIVSA-N (2R)-2-aminopentadecanoic acid Chemical group CCCCCCCCCCCCC[C@@H](N)C(O)=O XEDDSVXNGSVIKY-CQSZACIVSA-N 0.000 description 1
- RDFMDVXONNIGBC-ZCFIWIBFSA-N (2R)-aminoheptanoic acid Chemical group CCCCC[C@@H](N)C(O)=O RDFMDVXONNIGBC-ZCFIWIBFSA-N 0.000 description 1
- XRKBQVGBWJWJJJ-KRWDZBQOSA-N (2S)-2-aminooctadecanoic acid Chemical group CCCCCCCCCCCCCCCC[C@H](N)C(O)=O XRKBQVGBWJWJJJ-KRWDZBQOSA-N 0.000 description 1
- XEDDSVXNGSVIKY-AWEZNQCLSA-N (2S)-2-aminopentadecanoic acid Chemical group CCCCCCCCCCCCC[C@H](N)C(O)=O XEDDSVXNGSVIKY-AWEZNQCLSA-N 0.000 description 1
- JINGUCXQUOKWKH-SECBINFHSA-N (2r)-2-aminodecanoic acid Chemical group CCCCCCCC[C@@H](N)C(O)=O JINGUCXQUOKWKH-SECBINFHSA-N 0.000 description 1
- QUBNFZFTFXTLKH-LLVKDONJSA-N (2r)-2-aminododecanoic acid Chemical group CCCCCCCCCC[C@@H](N)C(O)=O QUBNFZFTFXTLKH-LLVKDONJSA-N 0.000 description 1
- BVXKPGXJOLWHFI-CYBMUJFWSA-N (2r)-2-aminotetradecanoic acid Chemical group CCCCCCCCCCCC[C@@H](N)C(O)=O BVXKPGXJOLWHFI-CYBMUJFWSA-N 0.000 description 1
- HASUJDLTAYUWCO-SNVBAGLBSA-N (2r)-2-aminoundecanoic acid Chemical group CCCCCCCCC[C@@H](N)C(O)=O HASUJDLTAYUWCO-SNVBAGLBSA-N 0.000 description 1
- JVPFOKXICYJJSC-MRVPVSSYSA-N (2r)-2-azaniumylnonanoate Chemical group CCCCCCC[C@@H]([NH3+])C([O-])=O JVPFOKXICYJJSC-MRVPVSSYSA-N 0.000 description 1
- JINGUCXQUOKWKH-VIFPVBQESA-N (2s)-2-aminodecanoic acid Chemical group CCCCCCCC[C@H](N)C(O)=O JINGUCXQUOKWKH-VIFPVBQESA-N 0.000 description 1
- QUBNFZFTFXTLKH-NSHDSACASA-N (2s)-2-aminododecanoic acid Chemical group CCCCCCCCCC[C@H](N)C(O)=O QUBNFZFTFXTLKH-NSHDSACASA-N 0.000 description 1
- CRJWOABTAHMMSA-INIZCTEOSA-N (2s)-2-aminoheptadecanoic acid Chemical group CCCCCCCCCCCCCCC[C@H](N)C(O)=O CRJWOABTAHMMSA-INIZCTEOSA-N 0.000 description 1
- BVXKPGXJOLWHFI-ZDUSSCGKSA-N (2s)-2-aminotetradecanoic acid Chemical group CCCCCCCCCCCC[C@H](N)C(O)=O BVXKPGXJOLWHFI-ZDUSSCGKSA-N 0.000 description 1
- HASUJDLTAYUWCO-JTQLQIEISA-N (2s)-2-aminoundecanoic acid Chemical group CCCCCCCCC[C@H](N)C(O)=O HASUJDLTAYUWCO-JTQLQIEISA-N 0.000 description 1
- JVPFOKXICYJJSC-QMMMGPOBSA-N (2s)-2-azaniumylnonanoate Chemical group CCCCCCC[C@H]([NH3+])C([O-])=O JVPFOKXICYJJSC-QMMMGPOBSA-N 0.000 description 1
- HSIUQCHVPSGZKT-UHFFFAOYSA-N 2-(methoxymethoxy)hexanoic acid Chemical group CCCCC(C(=O)O)OCOC HSIUQCHVPSGZKT-UHFFFAOYSA-N 0.000 description 1
- UNVRQZCTYCROLZ-UHFFFAOYSA-N 2-(methoxymethoxy)octadecanoic acid Chemical group CCCCCCCCCCCCCCCCC(C(O)=O)OCOC UNVRQZCTYCROLZ-UHFFFAOYSA-N 0.000 description 1
- SCDDPXCTSGNPLZ-UHFFFAOYSA-N 2-(methoxymethoxy)propanoic acid Chemical group COCOC(C)C(O)=O SCDDPXCTSGNPLZ-UHFFFAOYSA-N 0.000 description 1
- BVXKPGXJOLWHFI-UHFFFAOYSA-N 2-Amino-tetradecanoic acid Chemical group CCCCCCCCCCCCC(N)C(O)=O BVXKPGXJOLWHFI-UHFFFAOYSA-N 0.000 description 1
- MNRBGFKCVTVNBA-UHFFFAOYSA-N 2-Hydroxyundecanoate Chemical group CCCCCCCCCC(O)C(O)=O MNRBGFKCVTVNBA-UHFFFAOYSA-N 0.000 description 1
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical group CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 description 1
- CRJWOABTAHMMSA-UHFFFAOYSA-N 2-aminoheptadecanoic acid Chemical group CCCCCCCCCCCCCCCC(N)C(O)=O CRJWOABTAHMMSA-UHFFFAOYSA-N 0.000 description 1
- HASUJDLTAYUWCO-UHFFFAOYSA-N 2-aminoundecanoic acid Chemical group CCCCCCCCCC(N)C(O)=O HASUJDLTAYUWCO-UHFFFAOYSA-N 0.000 description 1
- JVPFOKXICYJJSC-UHFFFAOYSA-N 2-azaniumylnonanoate Chemical group CCCCCCCC(N)C(O)=O JVPFOKXICYJJSC-UHFFFAOYSA-N 0.000 description 1
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical group CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 description 1
- GHPVDCPCKSNJDR-UHFFFAOYSA-N 2-hydroxydecanoic acid Chemical group CCCCCCCCC(O)C(O)=O GHPVDCPCKSNJDR-UHFFFAOYSA-N 0.000 description 1
- YDZIJQXINJLRLL-UHFFFAOYSA-N 2-hydroxydodecanoic acid Chemical group CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 description 1
- KUZABABLVHWUGR-UHFFFAOYSA-N 2-hydroxyheptadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)C(O)=O KUZABABLVHWUGR-UHFFFAOYSA-N 0.000 description 1
- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical group CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical group CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical group CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- JKRDADVRIYVCCY-UHFFFAOYSA-N 2-hydroxyoctanoic acid Chemical group CCCCCCC(O)C(O)=O JKRDADVRIYVCCY-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- LGSNTPIHVYSXAV-UHFFFAOYSA-N tridec-2-ynoic acid Chemical group CCCCCCCCCCC#CC(O)=O LGSNTPIHVYSXAV-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57196248A JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
| DE8383306797T DE3371517D1 (de) | 1982-11-08 | 1983-11-08 | Novel ailanthone derivative |
| AT83306797T ATE27163T1 (de) | 1982-11-08 | 1983-11-08 | Aillanthonderivat. |
| EP83306797A EP0108645B1 (en) | 1982-11-08 | 1983-11-08 | Novel ailanthone derivative |
| US06/794,331 US4774342A (en) | 1982-11-08 | 1985-11-04 | Novel ailanthone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57196248A JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5984880A JPS5984880A (ja) | 1984-05-16 |
| JPH0354666B2 true JPH0354666B2 (bg) | 1991-08-20 |
Family
ID=16354645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57196248A Granted JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5984880A (bg) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6072882A (ja) * | 1983-09-29 | 1985-04-24 | Suntory Ltd | 新規アイラントン誘導体 |
| KR100872588B1 (ko) * | 2007-04-18 | 2008-12-08 | 대구한의대학교산학협력단 | 항산화 효과를 갖는 가죽나무 추출물을 유효성분으로함유하는 조성물 |
-
1982
- 1982-11-08 JP JP57196248A patent/JPS5984880A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5984880A (ja) | 1984-05-16 |
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