DE2200272A1 - Neue Zyklooctanonderivate mit guenstigen pharmakologischen Eigenschaften - Google Patents
Neue Zyklooctanonderivate mit guenstigen pharmakologischen EigenschaftenInfo
- Publication number
- DE2200272A1 DE2200272A1 DE19722200272 DE2200272A DE2200272A1 DE 2200272 A1 DE2200272 A1 DE 2200272A1 DE 19722200272 DE19722200272 DE 19722200272 DE 2200272 A DE2200272 A DE 2200272A DE 2200272 A1 DE2200272 A1 DE 2200272A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclooctanone
- substituents
- compound according
- benzyl
- methoxybenzyl
- 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.)
- Pending
Links
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical class O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 title claims description 48
- 230000000144 pharmacologic effect Effects 0.000 title description 2
- 230000002349 favourable effect Effects 0.000 title 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 alkoxy1 Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- QRZUPJILJVGUFF-UHFFFAOYSA-N 2,8-dibenzylcyclooctan-1-one Chemical group C1CCCCC(CC=2C=CC=CC=2)C(=O)C1CC1=CC=CC=C1 QRZUPJILJVGUFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- MMWYKSLZFXSEDF-UHFFFAOYSA-N N-(2-benzylcyclooctylidene)hydroxylamine Chemical group ON=C1CCCCCCC1CC1=CC=CC=C1 MMWYKSLZFXSEDF-UHFFFAOYSA-N 0.000 claims description 3
- IGOHANKAWZMALV-UHFFFAOYSA-N cyclooctanone;hydrochloride Chemical compound Cl.O=C1CCCCCCC1 IGOHANKAWZMALV-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 235000012000 cholesterol Nutrition 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- XVPYEGUVJMPSJN-UHFFFAOYSA-N 2-benzylcyclooctan-1-one Chemical class O=C1CCCCCCC1CC1=CC=CC=C1 XVPYEGUVJMPSJN-UHFFFAOYSA-N 0.000 description 4
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 4
- 206010003210 Arteriosclerosis Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
- BDCFUHIWJODVNG-UHFFFAOYSA-N Desmosterol Natural products C1C=C2CC(O)C=CC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BDCFUHIWJODVNG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ADVRWTWVDZKNFF-UHFFFAOYSA-N 2-benzylidenecyclooctan-1-one Chemical class O=C1CCCCCCC1=CC1=CC=CC=C1 ADVRWTWVDZKNFF-UHFFFAOYSA-N 0.000 description 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001840 cholesterol esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CYSNTYNRDDKJBV-NWILIBCHSA-N (2e,8e)-2,8-dibenzylidenecyclooctan-1-one Chemical compound O=C1\C(=C\C=2C=CC=CC=2)CCCCC\C1=C/C1=CC=CC=C1 CYSNTYNRDDKJBV-NWILIBCHSA-N 0.000 description 1
- ZHMAUBUXUJBAJG-UHFFFAOYSA-N 2,8-bis[(2-fluorophenyl)methyl]cyclooctan-1-one Chemical compound FC1=CC=CC=C1CC1C(=O)C(CC=2C(=CC=CC=2)F)CCCCC1 ZHMAUBUXUJBAJG-UHFFFAOYSA-N 0.000 description 1
- ZJTABBHLPWBXCV-UHFFFAOYSA-N 2,8-bis[(2-methylphenyl)methyl]cyclooctan-1-one Chemical compound CC1=CC=CC=C1CC1C(=O)C(CC=2C(=CC=CC=2)C)CCCCC1 ZJTABBHLPWBXCV-UHFFFAOYSA-N 0.000 description 1
- OYUWAJABZBQCBU-UHFFFAOYSA-N 2,8-bis[(3,4,5-trimethoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=C(OC)C(OC)=CC(CC2C(C(CC=3C=C(OC)C(OC)=C(OC)C=3)CCCCC2)=O)=C1 OYUWAJABZBQCBU-UHFFFAOYSA-N 0.000 description 1
- RLXQVDYHJXDXKU-UHFFFAOYSA-N 2,8-bis[(3,5-dichlorophenyl)methyl]cyclooctan-1-one Chemical compound ClC1=CC(Cl)=CC(CC2C(C(CC=3C=C(Cl)C=C(Cl)C=3)CCCCC2)=O)=C1 RLXQVDYHJXDXKU-UHFFFAOYSA-N 0.000 description 1
- XXPQIHBGJGPCFR-UHFFFAOYSA-N 2,8-bis[(3-hydroxyphenyl)methyl]cyclooctan-1-one Chemical compound OC1=CC=CC(CC2C(C(CC=3C=C(O)C=CC=3)CCCCC2)=O)=C1 XXPQIHBGJGPCFR-UHFFFAOYSA-N 0.000 description 1
- RHJBCLHYHHSPQX-UHFFFAOYSA-N 2,8-bis[(4-butylphenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(CCCC)=CC=C1CC1C(=O)C(CC=2C=CC(CCCC)=CC=2)CCCCC1 RHJBCLHYHHSPQX-UHFFFAOYSA-N 0.000 description 1
- ZHGCZEVWVPUPIU-UHFFFAOYSA-N 2,8-bis[(4-chlorophenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(Cl)=CC=C1CC1C(=O)C(CC=2C=CC(Cl)=CC=2)CCCCC1 ZHGCZEVWVPUPIU-UHFFFAOYSA-N 0.000 description 1
- LGUFHDOHVKLLOZ-UHFFFAOYSA-N 2,8-bis[(4-methoxyphenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(OC)=CC=C1CC1C(=O)C(CC=2C=CC(OC)=CC=2)CCCCC1 LGUFHDOHVKLLOZ-UHFFFAOYSA-N 0.000 description 1
- VOSUZUAKTXTQEL-UHFFFAOYSA-N 2,8-bis[[3-(trifluoromethyl)phenyl]methyl]cyclooctan-1-one Chemical compound FC(F)(F)C1=CC=CC(CC2C(C(CC=3C=C(C=CC=3)C(F)(F)F)CCCCC2)=O)=C1 VOSUZUAKTXTQEL-UHFFFAOYSA-N 0.000 description 1
- CYSNTYNRDDKJBV-UHFFFAOYSA-N 2,8-dibenzylidenecyclooctan-1-one Chemical class O=C1C(=CC=2C=CC=CC=2)CCCCCC1=CC1=CC=CC=C1 CYSNTYNRDDKJBV-UHFFFAOYSA-N 0.000 description 1
- LZDMKASYSQZZNL-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methyl]cyclooctan-1-one Chemical compound ClC1=CC=CC(CC2C(CCCCCC2)=O)=C1Cl LZDMKASYSQZZNL-UHFFFAOYSA-N 0.000 description 1
- PLYXSPWNBWBJPU-UHFFFAOYSA-N 2-[(2,3-dimethoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC=CC(CC2C(CCCCCC2)=O)=C1OC PLYXSPWNBWBJPU-UHFFFAOYSA-N 0.000 description 1
- ZSRKMOGNDWYNNM-UHFFFAOYSA-N 2-[(2,4,6-trimethoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC(OC)=CC(OC)=C1CC1C(=O)CCCCCC1 ZSRKMOGNDWYNNM-UHFFFAOYSA-N 0.000 description 1
- SEIBDPPWWZGXQT-UHFFFAOYSA-N 2-[(2,5-dihydroxyphenyl)methyl]cyclooctan-1-one Chemical compound OC1=CC=C(O)C(CC2C(CCCCCC2)=O)=C1 SEIBDPPWWZGXQT-UHFFFAOYSA-N 0.000 description 1
- XGSKUIROMJRROK-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]cyclooctan-1-one Chemical compound FC1=CC=CC=C1CC1C(=O)CCCCCC1 XGSKUIROMJRROK-UHFFFAOYSA-N 0.000 description 1
- IWKZKWGCPFCMIF-UHFFFAOYSA-N 2-[(2-hydroxy-4,6-dimethoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1CC1C(=O)CCCCCC1 IWKZKWGCPFCMIF-UHFFFAOYSA-N 0.000 description 1
- BRFZHEYQSYKXAY-UHFFFAOYSA-N 2-[(2-hydroxy-5-methoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC=C(O)C(CC2C(CCCCCC2)=O)=C1 BRFZHEYQSYKXAY-UHFFFAOYSA-N 0.000 description 1
- UUPNFHVNRAVCTP-UHFFFAOYSA-N 2-[(2-methylphenyl)methyl]cyclooctan-1-one Chemical compound CC1=CC=CC=C1CC1C(=O)CCCCCC1 UUPNFHVNRAVCTP-UHFFFAOYSA-N 0.000 description 1
- BIGHTHNRGFJMLZ-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]cyclooctan-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CC1C(=O)CCCCCC1 BIGHTHNRGFJMLZ-UHFFFAOYSA-N 0.000 description 1
- UVGLGJUNIIFLGN-UHFFFAOYSA-N 2-[(3,4-dihydroxyphenyl)methyl]cyclooctan-1-one Chemical compound C1=C(O)C(O)=CC=C1CC1C(=O)CCCCCC1 UVGLGJUNIIFLGN-UHFFFAOYSA-N 0.000 description 1
- ZNNOKGSNURVZLI-UHFFFAOYSA-N 2-[(3-aminophenyl)methyl]-8-[(2-fluorophenyl)methyl]cyclooctan-1-one Chemical compound NC1=CC=CC(CC2C(C(CC=3C(=CC=CC=3)F)CCCCC2)=O)=C1 ZNNOKGSNURVZLI-UHFFFAOYSA-N 0.000 description 1
- LITZDAHCWPWLBJ-UHFFFAOYSA-N 2-[(3-aminophenyl)methyl]cyclooctan-1-one Chemical compound NC1=CC=CC(CC2C(CCCCCC2)=O)=C1 LITZDAHCWPWLBJ-UHFFFAOYSA-N 0.000 description 1
- WHWDPJZCCLAMFK-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]cyclooctan-1-one Chemical compound FC1=CC=CC(CC2C(CCCCCC2)=O)=C1 WHWDPJZCCLAMFK-UHFFFAOYSA-N 0.000 description 1
- AELKVKOYPRQQMA-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC=CC(CC2C(CCCCCC2)=O)=C1 AELKVKOYPRQQMA-UHFFFAOYSA-N 0.000 description 1
- NIHZGCXLHFZYBP-UHFFFAOYSA-N 2-[(3-methylphenyl)methyl]cyclooctan-1-one Chemical compound CC1=CC=CC(CC2C(CCCCCC2)=O)=C1 NIHZGCXLHFZYBP-UHFFFAOYSA-N 0.000 description 1
- ZJANIUXCOQPFPK-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]-8-[(2-methoxyphenyl)methyl]cyclooctan-1-one Chemical compound COC1=CC=CC=C1CC1C(=O)C(CC=2C=CC(N)=CC=2)CCCCC1 ZJANIUXCOQPFPK-UHFFFAOYSA-N 0.000 description 1
- GSROCGPNZDZKOE-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]-8-[(3-chlorophenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(N)=CC=C1CC1C(=O)C(CC=2C=C(Cl)C=CC=2)CCCCC1 GSROCGPNZDZKOE-UHFFFAOYSA-N 0.000 description 1
- XSBIMRRPNREIRF-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]-8-[[4-(dimethylamino)phenyl]methyl]cyclooctan-1-one Chemical compound C1=CC(N(C)C)=CC=C1CC1C(=O)C(CC=2C=CC(N)=CC=2)CCCCC1 XSBIMRRPNREIRF-UHFFFAOYSA-N 0.000 description 1
- QQVCYTDKMCGWCP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]-8-benzylcyclooctan-1-one Chemical compound C1=CC(N)=CC=C1CC1C(=O)C(CC=2C=CC=CC=2)CCCCC1 QQVCYTDKMCGWCP-UHFFFAOYSA-N 0.000 description 1
- RIKBSRLZRQQHIG-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]-8-benzylcyclooctan-1-one;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1CC1C(=O)C(CC=2C=CC=CC=2)CCCCC1 RIKBSRLZRQQHIG-UHFFFAOYSA-N 0.000 description 1
- DSCOJJAOXCYCQB-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(Cl)=CC=C1CC1C(=O)CCCCCC1 DSCOJJAOXCYCQB-UHFFFAOYSA-N 0.000 description 1
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- CXEHAVGNFJINOH-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]cyclooctan-1-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)CCCCCC1 CXEHAVGNFJINOH-UHFFFAOYSA-N 0.000 description 1
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- UQUBQORJPHJFHC-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)phenyl]methyl]cyclooctan-1-one Chemical compound FC(F)(F)C1=CC=CC=C1CC1C(=O)CCCCCC1 UQUBQORJPHJFHC-UHFFFAOYSA-N 0.000 description 1
- DPBSGHGETPJUOW-UHFFFAOYSA-N 2-[[2-chloro-4-(dimethylamino)phenyl]methyl]cyclooctan-1-one Chemical compound ClC1=CC(N(C)C)=CC=C1CC1C(=O)CCCCCC1 DPBSGHGETPJUOW-UHFFFAOYSA-N 0.000 description 1
- IGNYUXGVNKXTNT-UHFFFAOYSA-N 2-[[3-(trifluoromethyl)phenyl]methyl]cyclooctan-1-one Chemical compound FC(F)(F)C1=CC=CC(CC2C(CCCCCC2)=O)=C1 IGNYUXGVNKXTNT-UHFFFAOYSA-N 0.000 description 1
- AZGRIEAJVFOQBO-UHFFFAOYSA-N 2-[[4-(dimethylamino)phenyl]methyl]cyclooctan-1-one Chemical compound C1=CC(N(C)C)=CC=C1CC1C(=O)CCCCCC1 AZGRIEAJVFOQBO-UHFFFAOYSA-N 0.000 description 1
- FGWXDDGELBICKB-UHFFFAOYSA-N 2-[[4-(methylamino)phenyl]methyl]cyclooctan-1-one Chemical compound C1=CC(NC)=CC=C1CC1C(=O)CCCCCC1 FGWXDDGELBICKB-UHFFFAOYSA-N 0.000 description 1
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- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
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- 238000007429 general method Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
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- 230000000260 hypercholesteremic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
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- 239000013067 intermediate product Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/51—Acetal radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10507671A | 1971-01-08 | 1971-01-08 | |
| US19844571A | 1971-11-12 | 1971-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2200272A1 true DE2200272A1 (de) | 1972-07-27 |
Family
ID=26802239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722200272 Pending DE2200272A1 (de) | 1971-01-08 | 1972-01-04 | Neue Zyklooctanonderivate mit guenstigen pharmakologischen Eigenschaften |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2200272A1 (enExample) |
| FR (1) | FR2121680A1 (enExample) |
| GB (1) | GB1339692A (enExample) |
-
1972
- 1972-01-04 DE DE19722200272 patent/DE2200272A1/de active Pending
- 1972-01-07 FR FR7200534A patent/FR2121680A1/fr not_active Withdrawn
- 1972-01-10 GB GB121872A patent/GB1339692A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2121680A1 (enExample) | 1972-08-25 |
| GB1339692A (en) | 1973-12-05 |
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