DE2752096A1 - Heterocyclische verbindungen - Google Patents
Heterocyclische verbindungenInfo
- Publication number
- DE2752096A1 DE2752096A1 DE19772752096 DE2752096A DE2752096A1 DE 2752096 A1 DE2752096 A1 DE 2752096A1 DE 19772752096 DE19772752096 DE 19772752096 DE 2752096 A DE2752096 A DE 2752096A DE 2752096 A1 DE2752096 A1 DE 2752096A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- phenyl
- propyl
- dimethyl
- piperidine
- 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.)
- Granted
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- -1 2-cyclohexyl-1,1-dimethyl-ethyl Chemical group 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000003795 chemical substances by application Substances 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 57
- 229910001868 water Inorganic materials 0.000 claims description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- 241000196324 Embryophyta Species 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000004965 peroxy acids Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- LFPUXEMYBDXHDX-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CCCCC1 LFPUXEMYBDXHDX-UHFFFAOYSA-N 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- QZZYBTXIHBEWHY-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]-3-methylbutyl]-3-methylpiperidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C(C)C)CN1CCCC(C)C1 QZZYBTXIHBEWHY-UHFFFAOYSA-N 0.000 claims description 3
- KPRUNUGGBCLJLU-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]-3-methylbutyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C(C)C)CN1CCCCC1 KPRUNUGGBCLJLU-UHFFFAOYSA-N 0.000 claims description 3
- AENWGVCFFZZIIX-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]decyl]-3-methylpiperidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(CCCCCCCC)CN1CCCC(C)C1 AENWGVCFFZZIIX-UHFFFAOYSA-N 0.000 claims description 3
- NXTZCGPBXWVOGR-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]decyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(CCCCCCCC)CN1CCCCC1 NXTZCGPBXWVOGR-UHFFFAOYSA-N 0.000 claims description 3
- DUFBVJPJOCEIJA-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]butyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)C(C)CN1CCCCC1 DUFBVJPJOCEIJA-UHFFFAOYSA-N 0.000 claims description 3
- VDDGOJGIVXFYKP-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]-1-oxidopiperidin-1-ium Chemical compound C1=CC(C(C)(C)CC)=CC=C1CC(C)C[N+]1([O-])CCCCC1 VDDGOJGIVXFYKP-UHFFFAOYSA-N 0.000 claims description 3
- FBCSGBBBIAWTOW-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylpropyl)phenyl]propyl]piperidine Chemical group C1=CC(CC(C)C)=CC=C1CC(C)CN1CCCCC1 FBCSGBBBIAWTOW-UHFFFAOYSA-N 0.000 claims description 3
- SGORDMPFPJLKCJ-UHFFFAOYSA-N 1-[3-(4-benzylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(CC=2C=CC=CC=2)C=CC=1CC(C)CN1CCCCC1 SGORDMPFPJLKCJ-UHFFFAOYSA-N 0.000 claims description 3
- HMKRERJVAPJZCA-UHFFFAOYSA-N 1-[3-[4-(2,2-dimethylpropyl)phenyl]-2-methylpropyl]piperidine Chemical group C=1C=C(CC(C)(C)C)C=CC=1CC(C)CN1CCCCC1 HMKRERJVAPJZCA-UHFFFAOYSA-N 0.000 claims description 3
- FVUPRJCEEAKDMM-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]butyl]morpholine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)C(C)CN1CC(C)OC(C)C1 FVUPRJCEEAKDMM-UHFFFAOYSA-N 0.000 claims description 3
- DIJLHVIUXUVKJZ-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]butyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)C(C)CN1CC(C)CC(C)C1 DIJLHVIUXUVKJZ-UHFFFAOYSA-N 0.000 claims description 3
- WDFZYGJYGHHWKX-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]propyl]piperidine Chemical group C1CC(C(C)(C)CC)CCC1CC(C)CN1CC(C)CCC1 WDFZYGJYGHHWKX-UHFFFAOYSA-N 0.000 claims description 3
- BUSBRROQWOGLIW-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]but-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)=C(C)CN1CC(C)CCC1 BUSBRROQWOGLIW-UHFFFAOYSA-N 0.000 claims description 3
- USIYNKQJTKKWAU-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]butyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)C(C)CN1CC(C)CCC1 USIYNKQJTKKWAU-UHFFFAOYSA-N 0.000 claims description 3
- DNHUCIPKCRHHEQ-UHFFFAOYSA-N 4-[3-(4-benzylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical group C=1C=C(CC=2C=CC=CC=2)C=CC=1CC(C)CN1CC(C)OC(C)C1 DNHUCIPKCRHHEQ-UHFFFAOYSA-N 0.000 claims description 3
- MTVSLAUNLQDDSY-UHFFFAOYSA-N 4-[3-[4-(2-cyclohexylpropan-2-yl)cyclohexyl]-2-methylpropyl]-2,6-dimethylmorpholine Chemical group C1C(C)OC(C)CN1CC(C)CC(CC1)CCC1C(C)(C)C1CCCCC1 MTVSLAUNLQDDSY-UHFFFAOYSA-N 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- AUDOISCMCZWWQS-UHFFFAOYSA-N 1-[2-methyl-3-(2-phenylphenyl)propyl]piperidine Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CC(C)CN1CCCCC1 AUDOISCMCZWWQS-UHFFFAOYSA-N 0.000 claims description 2
- CQMCGRBVKXQHHD-UHFFFAOYSA-N 1-[3-[4-(2-cyclohexylpropan-2-yl)cyclohexyl]-2-methylpropyl]piperidine Chemical compound C1CCCCN1CC(C)CC(CC1)CCC1C(C)(C)C1CCCCC1 CQMCGRBVKXQHHD-UHFFFAOYSA-N 0.000 claims description 2
- KLDAIXMRGIJTRO-UHFFFAOYSA-N 1-[3-[4-(3-ethylpentan-3-yl)phenyl]-2-methylpropyl]-3-methylpiperidine Chemical group C1=CC(C(CC)(CC)CC)=CC=C1CC(C)CN1CC(C)CCC1 KLDAIXMRGIJTRO-UHFFFAOYSA-N 0.000 claims description 2
- PFZATMMGUJCGCG-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-(4-phenylphenyl)propyl]morpholine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CC(C)CN1CC(C)OC(C)C1 PFZATMMGUJCGCG-UHFFFAOYSA-N 0.000 claims description 2
- BLKZAUAYNGFIEQ-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(4-methyloctan-4-yl)phenyl]propyl]morpholine Chemical group C1=CC(C(C)(CCC)CCCC)=CC=C1CC(C)CN1CC(C)OC(C)C1 BLKZAUAYNGFIEQ-UHFFFAOYSA-N 0.000 claims description 2
- BEDJMSXCTQDPGC-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CC(C)CC(C)C1 BEDJMSXCTQDPGC-UHFFFAOYSA-N 0.000 claims description 2
- XNMFBHJJUJHQBI-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CC(C)CCC1 XNMFBHJJUJHQBI-UHFFFAOYSA-N 0.000 claims description 2
- JZADWJLBMOCLCM-UHFFFAOYSA-N 4-[3-[4-(2,2-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(CC(C)(C)C)C=CC=1CC(C)CN1CC(C)OC(C)C1 JZADWJLBMOCLCM-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- YAWMOHFUKSUKIH-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]prop-2-enyl]piperidine Chemical compound C1CC(C(C)(C)CC)CCC1C=C(C)CN1CCCCC1 YAWMOHFUKSUKIH-UHFFFAOYSA-N 0.000 claims 2
- ZCNICAIECULHTO-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]propyl]piperidine Chemical group C1CC(C(C)(C)CC)CCC1CC(C)CN1CCCCC1 ZCNICAIECULHTO-UHFFFAOYSA-N 0.000 claims 2
- JBHFFCPGGUGXKQ-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]but-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)=C(C)CN1CCCCC1 JBHFFCPGGUGXKQ-UHFFFAOYSA-N 0.000 claims 2
- QVOBNMVTGOFWCH-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C=C(C)CN1CCCCC1 QVOBNMVTGOFWCH-UHFFFAOYSA-N 0.000 claims 2
- WMILIXDXZOSMRK-UHFFFAOYSA-N 1-[2-methyl-3-[4-(3-methylhexan-3-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(CC)CCC)=CC=C1CC(C)CN1CCCCC1 WMILIXDXZOSMRK-UHFFFAOYSA-N 0.000 claims 2
- URZXNRPRWWXZAI-UHFFFAOYSA-N 1-[3-(4-cyclohexylphenyl)-2-methylprop-2-enyl]piperidine Chemical group C=1C=C(C2CCCCC2)C=CC=1C=C(C)CN1CCCCC1 URZXNRPRWWXZAI-UHFFFAOYSA-N 0.000 claims 2
- SJVQHUZMQCOHRH-UHFFFAOYSA-N 1-[3-[4-(2,2-dimethylpropyl)phenyl]-2-methylpropyl]-3-methylpiperidine Chemical group C=1C=C(CC(C)(C)C)C=CC=1CC(C)CN1CCCC(C)C1 SJVQHUZMQCOHRH-UHFFFAOYSA-N 0.000 claims 2
- KHZQUMTUJOCWFO-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enyl]morpholine Chemical group C1=CC(C(C)(C)CC)=CC=C1C=C(C)CN1CC(C)OC(C)C1 KHZQUMTUJOCWFO-UHFFFAOYSA-N 0.000 claims 2
- FVSQRXVLXYEZIE-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(3-methylbutan-2-yl)phenyl]propyl]morpholine Chemical group C=1C=C(C(C)C(C)C)C=CC=1CC(C)CN1CC(C)OC(C)C1 FVSQRXVLXYEZIE-UHFFFAOYSA-N 0.000 claims 2
- RUUASXSDVSKAJB-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(3-methylhexan-3-yl)phenyl]propyl]morpholine Chemical group C1=CC(C(C)(CC)CCC)=CC=C1CC(C)CN1CC(C)OC(C)C1 RUUASXSDVSKAJB-UHFFFAOYSA-N 0.000 claims 2
- YUGHKWVRSSWMAG-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]prop-2-enyl]piperidine Chemical compound C1CC(C(C)(C)CC)CCC1C=C(C)CN1CC(C)CC(C)C1 YUGHKWVRSSWMAG-UHFFFAOYSA-N 0.000 claims 2
- BJVAYILKJZNJNH-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]propyl]piperidine Chemical group C1CC(C(C)(C)CC)CCC1CC(C)CN1CC(C)CC(C)C1 BJVAYILKJZNJNH-UHFFFAOYSA-N 0.000 claims 2
- XGRGTZNFLVAYKI-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]but-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)=C(C)CN1CC(C)CC(C)C1 XGRGTZNFLVAYKI-UHFFFAOYSA-N 0.000 claims 2
- VRXFJRFWQNOHGW-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C=C(C)CN1CC(C)CCC1 VRXFJRFWQNOHGW-UHFFFAOYSA-N 0.000 claims 2
- BNLRJPNQIOHJTJ-UHFFFAOYSA-N 4-[3-[4-(2,5-dimethylhexan-3-yl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine Chemical group C1=CC(C(C(C)C)CC(C)C)=CC=C1CC(C)CN1CC(C)OC(C)C1 BNLRJPNQIOHJTJ-UHFFFAOYSA-N 0.000 claims 2
- ANQUVNACUZARLU-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]butyl]-3-methylpiperidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(CC)CN1CCCC(C)C1 ANQUVNACUZARLU-UHFFFAOYSA-N 0.000 claims 1
- HECZLGQVKOOZLW-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]butyl]piperidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(CC)CN1CCCCC1 HECZLGQVKOOZLW-UHFFFAOYSA-N 0.000 claims 1
- BFXBKMGZNPTFOF-UHFFFAOYSA-N 1-[2-methyl-3-[4-(2-methylhexan-2-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(C)CCCC)=CC=C1CC(C)CN1CCCCC1 BFXBKMGZNPTFOF-UHFFFAOYSA-N 0.000 claims 1
- BRTMBRFUVMXJKA-UHFFFAOYSA-N 1-[2-methyl-3-[4-(4-methyloctan-4-yl)phenyl]propyl]piperidine Chemical compound C1=CC(C(C)(CCC)CCCC)=CC=C1CC(C)CN1CCCCC1 BRTMBRFUVMXJKA-UHFFFAOYSA-N 0.000 claims 1
- MBLKVTBLMZJAEQ-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]prop-2-enyl]morpholine Chemical group C1CC(C(C)(C)CC)CCC1C=C(C)CN1CC(C)OC(C)C1 MBLKVTBLMZJAEQ-UHFFFAOYSA-N 0.000 claims 1
- YZEXGCPMFPHDKH-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]propyl]morpholine Chemical group C1CC(C(C)(C)CC)CCC1CC(C)CN1CC(C)OC(C)C1 YZEXGCPMFPHDKH-UHFFFAOYSA-N 0.000 claims 1
- NDLHDFVYHZTHBP-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]but-2-enyl]morpholine Chemical group C1=CC(C(C)(C)CC)=CC=C1C(C)=C(C)CN1CC(C)OC(C)C1 NDLHDFVYHZTHBP-UHFFFAOYSA-N 0.000 claims 1
- MQHLMHIZUIDKOO-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical group C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CC(C)OC(C)C1 MQHLMHIZUIDKOO-UHFFFAOYSA-N 0.000 claims 1
- QNNWGFOSWYFXLS-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylpropyl)phenyl]propyl]morpholine Chemical compound C1=CC(CC(C)C)=CC=C1CC(C)CN1CC(C)OC(C)C1 QNNWGFOSWYFXLS-UHFFFAOYSA-N 0.000 claims 1
- PVDRSQDNZIQIAT-UHFFFAOYSA-N 3,5-dimethyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enyl]piperidine Chemical group C1=CC(C(C)(C)CC)=CC=C1C=C(C)CN1CC(C)CC(C)C1 PVDRSQDNZIQIAT-UHFFFAOYSA-N 0.000 claims 1
- ALMLRUPFLSSQEO-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-(2-phenylphenyl)propyl]piperidine Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CC(C)CN1CCCC(C)C1 ALMLRUPFLSSQEO-UHFFFAOYSA-N 0.000 claims 1
- MMCLDSSBDRSYOB-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylbutan-2-yl)cyclohexyl]prop-2-enyl]piperidine Chemical group C1CC(C(C)(C)CC)CCC1C=C(C)CN1CC(C)CCC1 MMCLDSSBDRSYOB-UHFFFAOYSA-N 0.000 claims 1
- ZOTDOUJAFWGRQR-UHFFFAOYSA-N 3-methyl-1-[2-methyl-3-[4-(2-methylhexan-2-yl)phenyl]propyl]piperidine Chemical group C1=CC(C(C)(C)CCCC)=CC=C1CC(C)CN1CC(C)CCC1 ZOTDOUJAFWGRQR-UHFFFAOYSA-N 0.000 claims 1
- NHMXWYDIHMLDBD-UHFFFAOYSA-N 4-[3-[4-(1-cyclohexyl-2-methylpropan-2-yl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)CC2CCCCC2)C=CC=1CC(C)CN1CC(C)OC(C)C1 NHMXWYDIHMLDBD-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 description 43
- 239000004480 active ingredient Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 27
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 210000005000 reproductive tract Anatomy 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- RCIJACVHOIKRAP-UHFFFAOYSA-N sodium;1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound [Na+].CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC RCIJACVHOIKRAP-UHFFFAOYSA-N 0.000 description 1
- 239000004071 soot 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
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940044977 vaginal tablet Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/23—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde polycyclic
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Veterinary Medicine (AREA)
- Insects & Arthropods (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT866076A AT354187B (de) | 1976-11-22 | 1976-11-22 | Fungizides mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2752096A1 true DE2752096A1 (de) | 1978-06-01 |
| DE2752096C2 DE2752096C2 (enExample) | 1990-04-12 |
Family
ID=3607468
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2752135A Expired DE2752135C2 (de) | 1976-11-22 | 1977-11-22 | Heterocyclische Verbindungen |
| DE19772752096 Granted DE2752096A1 (de) | 1976-11-22 | 1977-11-22 | Heterocyclische verbindungen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2752135A Expired DE2752135C2 (de) | 1976-11-22 | 1977-11-22 | Heterocyclische Verbindungen |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US4202894A (enExample) |
| JP (3) | JPS6026105B2 (enExample) |
| AR (1) | AR223455A1 (enExample) |
| AT (1) | AT354187B (enExample) |
| AU (2) | AU515309B2 (enExample) |
| BE (2) | BE861002A (enExample) |
| CA (2) | CA1107282A (enExample) |
| CH (6) | CH633263A5 (enExample) |
| DE (2) | DE2752135C2 (enExample) |
| DK (2) | DK153544C (enExample) |
| EG (1) | EG13149A (enExample) |
| ES (6) | ES464324A1 (enExample) |
| FR (2) | FR2371436A1 (enExample) |
| GB (2) | GB1584290A (enExample) |
| HU (2) | HU181881B (enExample) |
| IE (2) | IE45913B1 (enExample) |
| IL (2) | IL53411A (enExample) |
| IT (2) | IT1143779B (enExample) |
| KE (1) | KE3144A (enExample) |
| LU (2) | LU78549A1 (enExample) |
| MC (2) | MC1170A1 (enExample) |
| NL (2) | NL174350C (enExample) |
| NZ (2) | NZ185700A (enExample) |
| PL (4) | PL202309A1 (enExample) |
| SE (2) | SE437022B (enExample) |
| SU (2) | SU702992A3 (enExample) |
| TR (2) | TR19533A (enExample) |
| ZA (2) | ZA776820B (enExample) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000333A3 (en) * | 1977-06-18 | 1979-07-25 | Basf Aktiengesellschaft | Cyclic amine derivatives and fungicides containing them |
| EP0006992A1 (de) * | 1978-06-14 | 1980-01-23 | BASF Aktiengesellschaft | 3-(p-Isopropyl-phenyl)-2-methyl-n-propyl-amine, diese enthaltende Fungizide, ein Verfahren zur Herstellung der genannten Verbindungen und Verfahren zur Bekämpfung von Pilzen unter Verwendung der genannten Verbindungen |
| EP0007479A1 (de) * | 1978-07-08 | 1980-02-06 | BASF Aktiengesellschaft | N-Arylpropyl-substituierte cyclische Amine, Fungizide, die diese Verbindungen enthalten und Verfahren zu ihrer Herstellung |
| US4283534A (en) | 1979-04-11 | 1981-08-11 | Basf Aktiengesellschaft | Reductive alkylation of nitrogen heterocycles |
| EP0031114A3 (en) * | 1979-12-24 | 1981-11-11 | Basf Aktiengesellschaft | Phenylpropyl ammonium salts, process for their preparation and agents containing these compounds |
| EP0056461A1 (de) * | 1981-01-16 | 1982-07-28 | BASF Aktiengesellschaft | N-3'-(p-tertiär-Butylphenyl)-2'-methyl-propyl-1'-piperidin-derivate, diese enthaltende Fungizide und Verfahren zur Bekämpfung von Pilzen mit diesen Verbindungen |
| EP0024334B1 (de) * | 1979-08-17 | 1983-07-20 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Neue Morpholinderivate, Verfahren zu deren Herstellung, diese Derivate enthaltende pharmazeutische Präparate |
| US4410734A (en) | 1980-01-16 | 1983-10-18 | Basf Aktiengesellschaft | Optically active phenylpropane derivatives, their preparation and their use for the preparation of fungicides |
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| DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
| DE2830120A1 (de) * | 1978-07-08 | 1980-01-17 | Basf Ag | Substituierte phenylpropylhalogenide |
| DE2830999A1 (de) * | 1978-07-14 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von stereoisomeren n-aralkyl-2,6-dimethylmorpholinen |
| ATE3111T1 (de) * | 1978-08-08 | 1983-05-15 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Verfahren zur herstellung von phenyl-propylmorpholin- und -piperidin-derivaten. |
| DE2921221A1 (de) * | 1979-05-25 | 1980-12-11 | Basf Ag | Trans-3-(4'-tert.-butyl-cyclohexyl-1')- 2-methyl-1-(3'-methylpiperidino, 3', 5'- dimethylpiperidino und 2', 6'-dimethylmorpholino)-propan, verfahren zu ihrer reinherstellung und diese enthaltende antimykotische mittel |
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| CH644113A5 (en) * | 1979-08-17 | 1984-07-13 | Hoffmann La Roche | N-substituted 2,6-dimethylmorpholine compounds |
| DE3001581A1 (de) * | 1980-01-17 | 1981-07-23 | Basf Ag, 6700 Ludwigshafen | Substituierte n- (3(4'-tert-butyl-cyclohex-1'-en1'yl)-2-methyl-propyl-1) -cycloalkalamine, ihre herstellung und ihre anwendung als fungizide |
| JPS5791905A (en) * | 1980-09-30 | 1982-06-08 | Hoffmann La Roche | Fungicidal composition |
| US4434165A (en) | 1980-09-30 | 1984-02-28 | Hoffmann-La Roche Inc. | Fungicidal compositions |
| FR2503705A1 (fr) * | 1981-04-14 | 1982-10-15 | Synthelabo | Derives de phenethanolamine, leur preparation et leur application en therapeutique |
| DE3134220A1 (de) * | 1981-08-29 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Phenylpropylammoniumsalz enthaltende fungizide und verfahren zur bekaempfung von pilzen |
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| DE3321712A1 (de) * | 1983-06-16 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | 2,6-trans-dimethylmorpholinderivate und diese enthaltende fungizide und verfahren zur bekaempfung von pilzen |
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| BR0307912B1 (pt) * | 2002-03-01 | 2013-12-03 | Mistura fungicida, método para combater fungos nocivos, e, agente fungicida | |
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Cited By (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000333A3 (en) * | 1977-06-18 | 1979-07-25 | Basf Aktiengesellschaft | Cyclic amine derivatives and fungicides containing them |
| EP0006992A1 (de) * | 1978-06-14 | 1980-01-23 | BASF Aktiengesellschaft | 3-(p-Isopropyl-phenyl)-2-methyl-n-propyl-amine, diese enthaltende Fungizide, ein Verfahren zur Herstellung der genannten Verbindungen und Verfahren zur Bekämpfung von Pilzen unter Verwendung der genannten Verbindungen |
| EP0007479A1 (de) * | 1978-07-08 | 1980-02-06 | BASF Aktiengesellschaft | N-Arylpropyl-substituierte cyclische Amine, Fungizide, die diese Verbindungen enthalten und Verfahren zu ihrer Herstellung |
| US4283534A (en) | 1979-04-11 | 1981-08-11 | Basf Aktiengesellschaft | Reductive alkylation of nitrogen heterocycles |
| EP0024334B1 (de) * | 1979-08-17 | 1983-07-20 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Neue Morpholinderivate, Verfahren zu deren Herstellung, diese Derivate enthaltende pharmazeutische Präparate |
| US4554006A (en) * | 1979-12-24 | 1985-11-19 | Basf Aktiengesellschaft | Phenylpropylammonium salts, their manufacture and agents containing these compounds |
| EP0031114A3 (en) * | 1979-12-24 | 1981-11-11 | Basf Aktiengesellschaft | Phenylpropyl ammonium salts, process for their preparation and agents containing these compounds |
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