JPH0210133B2 - - Google Patents
Info
- Publication number
- JPH0210133B2 JPH0210133B2 JP54115240A JP11524079A JPH0210133B2 JP H0210133 B2 JPH0210133 B2 JP H0210133B2 JP 54115240 A JP54115240 A JP 54115240A JP 11524079 A JP11524079 A JP 11524079A JP H0210133 B2 JPH0210133 B2 JP H0210133B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- cyclohexane
- formula
- dione
- general 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 14
- 239000004480 active ingredient Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy groups Chemical group 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- KYDUFZZSUUSMLF-UHFFFAOYSA-N 5-phenyl-2-(2-phenylacetyl)cyclohexane-1,3-dione Chemical compound O=C1CC(C=2C=CC=CC=2)CC(=O)C1C(=O)CC1=CC=CC=C1 KYDUFZZSUUSMLF-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VLTPLHUDHMOWRM-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O VLTPLHUDHMOWRM-UHFFFAOYSA-N 0.000 description 4
- DFCDIXCOBCHSEF-UHFFFAOYSA-N 5-phenyl-2-[2-(4-phenylmethoxyphenyl)acetyl]cyclohexane-1,3-dione Chemical compound O=C1CC(C=2C=CC=CC=2)CC(=O)C1C(=O)CC(C=C1)=CC=C1OCC1=CC=CC=C1 DFCDIXCOBCHSEF-UHFFFAOYSA-N 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000007530 Essential hypertension Diseases 0.000 description 4
- 229920000084 Gum arabic Polymers 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- 239000002220 antihypertensive agent Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OXMGPKCKUIMZOR-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(O)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O OXMGPKCKUIMZOR-UHFFFAOYSA-N 0.000 description 3
- MSEFVCLFWHFBOY-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-2-[3-(3,4-dihydroxyphenyl)propanoyl]cyclohexane-1,3-dione Chemical compound C1=C(O)C(O)=CC=C1CCC(=O)C1C(=O)CC(C=2C=C3OCOC3=CC=2)CC1=O MSEFVCLFWHFBOY-UHFFFAOYSA-N 0.000 description 3
- FNCGHZSZJKGTNA-UHFFFAOYSA-N 5-phenyl-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound O=C1CC(C=2C=CC=CC=2)CC(=O)C1C(=O)CCC1=CC=CC=C1 FNCGHZSZJKGTNA-UHFFFAOYSA-N 0.000 description 3
- UPPYKNLSSLIIAZ-UHFFFAOYSA-N 5-phenylcyclohexane-1,3-dione Chemical compound C1C(=O)CC(=O)CC1C1=CC=CC=C1 UPPYKNLSSLIIAZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001934 cyclohexanes Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- MMMKTCZKAGTYHM-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound ClC1=CC(Cl)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O MMMKTCZKAGTYHM-UHFFFAOYSA-N 0.000 description 2
- RSYXHMYULDFTCO-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)acetyl]-5-(furan-2-yl)cyclohexane-1,3-dione Chemical compound ClC1=CC=CC=C1CC(=O)C1C(=O)CC(C=2OC=CC=2)CC1=O RSYXHMYULDFTCO-UHFFFAOYSA-N 0.000 description 2
- HKZOYDBEQHCNQU-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound ClC1=CC=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O HKZOYDBEQHCNQU-UHFFFAOYSA-N 0.000 description 2
- IYDDBPUYXJWBLA-UHFFFAOYSA-N 2-[2-(2-hydroxy-3-methoxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound COC1=CC=CC(CC(=O)C2C(CC(CC2=O)C=2C=CC=CC=2)=O)=C1O IYDDBPUYXJWBLA-UHFFFAOYSA-N 0.000 description 2
- HJCQIDKZACSLCN-UHFFFAOYSA-N 2-[2-(2-hydroxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound OC1=CC=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O HJCQIDKZACSLCN-UHFFFAOYSA-N 0.000 description 2
- APUNBNQIPZFUMS-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound COC1=CC=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O APUNBNQIPZFUMS-UHFFFAOYSA-N 0.000 description 2
- SNZFMTHYDMCGNS-UHFFFAOYSA-N 2-[2-(2-nitrophenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O SNZFMTHYDMCGNS-UHFFFAOYSA-N 0.000 description 2
- GXIRNIPHAVEFQU-UHFFFAOYSA-N 2-[2-(3-methoxy-2-phenylmethoxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound C=1C=CC=CC=1COC=1C(OC)=CC=CC=1CC(=O)C(C(C1)=O)C(=O)CC1C1=CC=CC=C1 GXIRNIPHAVEFQU-UHFFFAOYSA-N 0.000 description 2
- GWUNEKDUVRKMFB-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)acetyl]-5-(furan-2-yl)cyclohexane-1,3-dione Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1C(=O)CC(C=2OC=CC=2)CC1=O GWUNEKDUVRKMFB-UHFFFAOYSA-N 0.000 description 2
- XQPBXDIDBJZLGQ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O XQPBXDIDBJZLGQ-UHFFFAOYSA-N 0.000 description 2
- GSBFDXNSNYMEDU-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O GSBFDXNSNYMEDU-UHFFFAOYSA-N 0.000 description 2
- JTFQAIQUDUVIHN-UHFFFAOYSA-N 2-[2-(4-methylphenyl)acetyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(C)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O JTFQAIQUDUVIHN-UHFFFAOYSA-N 0.000 description 2
- IURSSHYHFLAWNS-UHFFFAOYSA-N 2-[3-(2,4-dichlorophenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound ClC1=CC(Cl)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O IURSSHYHFLAWNS-UHFFFAOYSA-N 0.000 description 2
- UBQXNCGUDXCQPM-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)propanoyl]-5-(4-methoxyphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1C1CC(=O)C(C(=O)CCC=2C(=CC=CC=2)Cl)C(=O)C1 UBQXNCGUDXCQPM-UHFFFAOYSA-N 0.000 description 2
- YSEWEYYWWXKJNQ-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)propanoyl]-5-(4-methylphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(C)=CC=C1C1CC(=O)C(C(=O)CCC=2C(=CC=CC=2)Cl)C(=O)C1 YSEWEYYWWXKJNQ-UHFFFAOYSA-N 0.000 description 2
- BPGMHZSOIBKFQW-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound ClC1=CC=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O BPGMHZSOIBKFQW-UHFFFAOYSA-N 0.000 description 2
- XKWVRDXQDDBOSH-UHFFFAOYSA-N 2-[3-(2-fluorophenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound FC1=CC=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O XKWVRDXQDDBOSH-UHFFFAOYSA-N 0.000 description 2
- BNNAOHLMVXGWHF-UHFFFAOYSA-N 2-[3-(2-hydroxy-3-methoxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound COC1=CC=CC(CCC(=O)C2C(CC(CC2=O)C=2C=CC=CC=2)=O)=C1O BNNAOHLMVXGWHF-UHFFFAOYSA-N 0.000 description 2
- ATRVVDUGKFSVBB-UHFFFAOYSA-N 2-[3-(3,4-dihydroxyphenyl)propanoyl]-5-(2-methoxyphenyl)cyclohexane-1,3-dione Chemical compound COC1=CC=CC=C1C1CC(=O)C(C(=O)CCC=2C=C(O)C(O)=CC=2)C(=O)C1 ATRVVDUGKFSVBB-UHFFFAOYSA-N 0.000 description 2
- OLGJRFHLHBQDKJ-UHFFFAOYSA-N 2-[3-(3,4-dihydroxyphenyl)propanoyl]-5-(4-methoxyphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1C1CC(=O)C(C(=O)CCC=2C=C(O)C(O)=CC=2)C(=O)C1 OLGJRFHLHBQDKJ-UHFFFAOYSA-N 0.000 description 2
- UXHUVDKRAJUZOU-UHFFFAOYSA-N 2-[3-(3,4-dihydroxyphenyl)propanoyl]-5-(4-methylphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(C)=CC=C1C1CC(=O)C(C(=O)CCC=2C=C(O)C(O)=CC=2)C(=O)C1 UXHUVDKRAJUZOU-UHFFFAOYSA-N 0.000 description 2
- URUWPADSGSSJEO-UHFFFAOYSA-N 2-[3-(3,4-dihydroxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=C(O)C(O)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O URUWPADSGSSJEO-UHFFFAOYSA-N 0.000 description 2
- GAJYRXRQPSVQDH-UHFFFAOYSA-N 2-[3-(3,4-dimethoxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=C(OC)C(OC)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O GAJYRXRQPSVQDH-UHFFFAOYSA-N 0.000 description 2
- HZSNNANFPCWKIP-UHFFFAOYSA-N 2-[3-(3-hydroxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound OC1=CC=CC(CCC(=O)C2C(CC(CC2=O)C=2C=CC=CC=2)=O)=C1 HZSNNANFPCWKIP-UHFFFAOYSA-N 0.000 description 2
- FVEXZQNRVBACAU-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propanoyl]-5-(4-methoxyphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1C1CC(=O)C(C(=O)CCC=2C=CC(Cl)=CC=2)C(=O)C1 FVEXZQNRVBACAU-UHFFFAOYSA-N 0.000 description 2
- ASHCLDTWWRKADD-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(Cl)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O ASHCLDTWWRKADD-UHFFFAOYSA-N 0.000 description 2
- XUUYHIJSEUGHTQ-UHFFFAOYSA-N 2-[3-(4-ethoxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(OCC)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O XUUYHIJSEUGHTQ-UHFFFAOYSA-N 0.000 description 2
- IPROUOVGSHDDDH-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(O)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O IPROUOVGSHDDDH-UHFFFAOYSA-N 0.000 description 2
- AZQHPNFLXVBRNS-UHFFFAOYSA-N 2-[3-(4-methylphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(C)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O AZQHPNFLXVBRNS-UHFFFAOYSA-N 0.000 description 2
- CKKIBOHPBPVOGZ-UHFFFAOYSA-N 2-[3-(4-methylsulfonylphenyl)propanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O CKKIBOHPBPVOGZ-UHFFFAOYSA-N 0.000 description 2
- JJQMWKNPBACGQH-UHFFFAOYSA-N 2-[4-(2,4-dihydroxyphenyl)butanoyl]-5-phenylcyclohexane-1,3-dione Chemical compound OC1=CC(O)=CC=C1CCCC(=O)C1C(=O)CC(C=2C=CC=CC=2)CC1=O JJQMWKNPBACGQH-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- HSESRVLEWIGDBK-UHFFFAOYSA-N 4-[3-(2,6-dioxo-4-phenylcyclohexyl)-3-oxopropyl]benzonitrile Chemical compound O=C1CC(C=2C=CC=CC=2)CC(=O)C1C(=O)CCC1=CC=C(C#N)C=C1 HSESRVLEWIGDBK-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- DQHPLDCQRNWFKW-UHFFFAOYSA-N 5-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound O=C1CC(C=2C=C3OCCOC3=CC=2)CC(=O)C1C(=O)CCC1=CC=CC=C1 DQHPLDCQRNWFKW-UHFFFAOYSA-N 0.000 description 2
- NIAHYFYSWQMRTG-UHFFFAOYSA-N 5-(2-methoxyphenyl)-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound COC1=CC=CC=C1C1CC(=O)C(C(=O)CCC=2C=CC=CC=2)C(=O)C1 NIAHYFYSWQMRTG-UHFFFAOYSA-N 0.000 description 2
- PGRMKWHLFGAOAS-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1C1CC(=O)C(C(=O)CCC=2C=CC=CC=2)C(=O)C1 PGRMKWHLFGAOAS-UHFFFAOYSA-N 0.000 description 2
- QTJKGWVFWDQRQB-UHFFFAOYSA-N 5-(3,4-dihydroxyphenyl)-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound C1=C(O)C(O)=CC=C1C1CC(=O)C(C(=O)CCC=2C=CC=CC=2)C(=O)C1 QTJKGWVFWDQRQB-UHFFFAOYSA-N 0.000 description 2
- ITCHVOFQRGETCN-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-2-(3-phenylpropanoyl)cyclohexane-1,3-dione Chemical compound OC1=CC=CC(C2CC(=O)C(C(=O)CCC=3C=CC=CC=3)C(=O)C2)=C1 ITCHVOFQRGETCN-UHFFFAOYSA-N 0.000 description 2
- PXKDWMGFLYLFSG-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-(2-phenylacetyl)cyclohexane-1,3-dione Chemical compound C1=CC(Cl)=CC=C1C1CC(=O)C(C(=O)CC=2C=CC=CC=2)C(=O)C1 PXKDWMGFLYLFSG-UHFFFAOYSA-N 0.000 description 2
- GUNNQVQHIIQYDK-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-(2-chlorophenyl)acetyl]cyclohexane-1,3-dione Chemical compound C1=CC(Cl)=CC=C1C1CC(=O)C(C(=O)CC=2C(=CC=CC=2)Cl)C(=O)C1 GUNNQVQHIIQYDK-UHFFFAOYSA-N 0.000 description 2
- GRPQZUYNRFTSQQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-(4-methoxyphenyl)acetyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1CC(=O)C1C(=O)CC(C=2C=CC(Cl)=CC=2)CC1=O GRPQZUYNRFTSQQ-UHFFFAOYSA-N 0.000 description 2
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- 239000007902 hard capsule Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 201000005857 malignant hypertension Diseases 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11524079A JPS5640634A (en) | 1979-09-10 | 1979-09-10 | Cyclohexane derivative, its preparation, and pharmaceutical containing the same |
| US06/133,694 US4350705A (en) | 1979-03-31 | 1980-03-25 | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
| EP80101685A EP0017195B1 (de) | 1979-03-31 | 1980-03-28 | Derivate von 2,5-disubstituierten Cyclohexan-1,3-dionen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzung |
| DE8080101685T DE3068412D1 (en) | 1979-03-31 | 1980-03-28 | Derivatives of 2,5-disubstituted-cyclohexane-1,3-diones, process for preparation thereof and pharmaceutical composition containing them |
| US06/362,358 US4421763A (en) | 1979-03-31 | 1982-03-26 | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11524079A JPS5640634A (en) | 1979-09-10 | 1979-09-10 | Cyclohexane derivative, its preparation, and pharmaceutical containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5640634A JPS5640634A (en) | 1981-04-16 |
| JPH0210133B2 true JPH0210133B2 (de) | 1990-03-06 |
Family
ID=14657807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11524079A Granted JPS5640634A (en) | 1979-03-31 | 1979-09-10 | Cyclohexane derivative, its preparation, and pharmaceutical containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5640634A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832850A (de) * | 1971-09-02 | 1973-05-02 | ||
| JPS4943951A (de) * | 1972-09-01 | 1974-04-25 | ||
| JPS511633A (ja) * | 1974-06-25 | 1976-01-08 | Toray Industries | Noengeiyosatsukinzai |
-
1979
- 1979-09-10 JP JP11524079A patent/JPS5640634A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832850A (de) * | 1971-09-02 | 1973-05-02 | ||
| JPS4943951A (de) * | 1972-09-01 | 1974-04-25 | ||
| JPS511633A (ja) * | 1974-06-25 | 1976-01-08 | Toray Industries | Noengeiyosatsukinzai |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5640634A (en) | 1981-04-16 |
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