NO743281L - - Google Patents
Info
- Publication number
- NO743281L NO743281L NO743281A NO743281A NO743281L NO 743281 L NO743281 L NO 743281L NO 743281 A NO743281 A NO 743281A NO 743281 A NO743281 A NO 743281A NO 743281 L NO743281 L NO 743281L
- Authority
- NO
- Norway
- Prior art keywords
- cyclopropyl
- formula
- methyl
- derivative
- chlorophenyl
- Prior art date
Links
- -1 alkyl radical Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 10
- UUQYPFQAGUZHME-UHFFFAOYSA-N 2-cyclopropyl-1-phenylpyrrolidine Chemical class C1CC1C1N(C=2C=CC=CC=2)CCC1 UUQYPFQAGUZHME-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- LTNRJUDZKFOCFJ-UHFFFAOYSA-N 1-nitropentan-2-one Chemical compound CCCC(=O)C[N+]([O-])=O LTNRJUDZKFOCFJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- OIPDQFASJNLEME-UHFFFAOYSA-N 1-cyclopropyl-3-phenylprop-2-en-1-one Chemical compound C1CC1C(=O)C=CC1=CC=CC=C1 OIPDQFASJNLEME-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005882 aldol condensation reaction Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- BVALZCVRLDMXOQ-UHFFFAOYSA-N 1-nitropentane Chemical compound CCCCC[N+]([O-])=O BVALZCVRLDMXOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 238000006845 Michael addition reaction Methods 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 25
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- 238000001953 recrystallisation Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229940025084 amphetamine Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XSMQQWCXAFQJQR-UHFFFAOYSA-N 1-cyclopropyl-3-(3-fluorophenyl)prop-2-en-1-one Chemical compound FC1=CC=CC(C=CC(=O)C2CC2)=C1 XSMQQWCXAFQJQR-UHFFFAOYSA-N 0.000 description 3
- ZWDLYHWRZIDUQK-UHFFFAOYSA-N 1-cyclopropyl-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)C2CC2)=C1 ZWDLYHWRZIDUQK-UHFFFAOYSA-N 0.000 description 3
- XMTMVWXLOFJOOP-UHFFFAOYSA-N 1-cyclopropyl-4-nitro-3-phenylpentan-2-one Chemical compound C=1C=CC=CC=1C(C(C)[N+]([O-])=O)C(=O)CC1CC1 XMTMVWXLOFJOOP-UHFFFAOYSA-N 0.000 description 3
- FJKAJRHGUNEXQL-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-cyclopropyl-4-nitropentan-2-one Chemical compound C=1C=CC(Cl)=CC=1C(C(C)[N+]([O-])=O)C(=O)CC1CC1 FJKAJRHGUNEXQL-UHFFFAOYSA-N 0.000 description 3
- HBYNZTAHWAWILN-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-cyclopropylprop-2-en-1-one Chemical compound ClC1=CC=CC(C=CC(=O)C2CC2)=C1 HBYNZTAHWAWILN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 230000002891 anorexigenic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GGNNHEOQTQZJOY-UHFFFAOYSA-N 1-cyclopropyl-3-(3-fluorophenyl)-4-methyl-4-nitropentan-2-one Chemical compound C=1C=CC(F)=CC=1C(C(C)(C)[N+]([O-])=O)C(=O)CC1CC1 GGNNHEOQTQZJOY-UHFFFAOYSA-N 0.000 description 2
- MSBYJZPERVLUGT-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methylphenyl)-4-nitropentan-2-one Chemical compound C=1C=C(C)C=CC=1C(C(C)[N+]([O-])=O)C(=O)CC1CC1 MSBYJZPERVLUGT-UHFFFAOYSA-N 0.000 description 2
- LKBIRMBXFXJWPN-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-cyclopropyl-4-methyl-4-nitropentan-2-one Chemical compound C=1C=CC(Cl)=CC=1C(C(C)(C)[N+]([O-])=O)C(=O)CC1CC1 LKBIRMBXFXJWPN-UHFFFAOYSA-N 0.000 description 2
- ITEWHRQJLMFLRW-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-cyclopropyl-4-nitropentan-2-one Chemical compound C=1C=C(Cl)C=CC=1C(C(C)[N+]([O-])=O)C(=O)CC1CC1 ITEWHRQJLMFLRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 1
- OIPDQFASJNLEME-RMKNXTFCSA-N (e)-1-cyclopropyl-3-phenylprop-2-en-1-one Chemical compound C1CC1C(=O)\C=C\C1=CC=CC=C1 OIPDQFASJNLEME-RMKNXTFCSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RRDXMTMIVRPUEH-UHFFFAOYSA-N 1-cyclopropyl-3-(3,4-dichlorophenyl)-4-nitropentan-2-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(C)[N+]([O-])=O)C(=O)CC1CC1 RRDXMTMIVRPUEH-UHFFFAOYSA-N 0.000 description 1
- MQUOARGIVDGAGH-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methylphenyl)prop-2-en-1-one Chemical compound C1=CC(C)=CC=C1C=CC(=O)C1CC1 MQUOARGIVDGAGH-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000000578 anorexic effect Effects 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- OEDMOCYNWLHUDP-UHFFFAOYSA-N bromomethanol Chemical compound OCBr OEDMOCYNWLHUDP-UHFFFAOYSA-N 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- CLUPOLFGIGLMIQ-UHFFFAOYSA-N heptane;propan-2-ol Chemical compound CC(C)O.CCCCCCC CLUPOLFGIGLMIQ-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000021231 nutrient uptake Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- SUMPVOWEIHBNQO-UHFFFAOYSA-N pentane;propan-2-ol Chemical compound CC(C)O.CCCCC SUMPVOWEIHBNQO-UHFFFAOYSA-N 0.000 description 1
- PZJBWSQQDMRZHY-UHFFFAOYSA-N picilorex Chemical compound CC1NC(C2CC2)CC1C1=CC=C(Cl)C=C1 PZJBWSQQDMRZHY-UHFFFAOYSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 208000037905 systemic hypertension Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C45/61—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4539573A GB1474907A (en) | 1973-09-27 | 1973-09-27 | Pyrolidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO743281L true NO743281L (xx) | 1975-04-28 |
Family
ID=10437065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743281A NO743281L (xx) | 1973-09-27 | 1974-09-12 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4005103A (xx) |
| JP (1) | JPS5076052A (xx) |
| AR (1) | AR209281A1 (xx) |
| AT (1) | AT336601B (xx) |
| BE (1) | BE820191A (xx) |
| CA (1) | CA1025456A (xx) |
| CH (1) | CH593255A5 (xx) |
| CS (1) | CS188203B2 (xx) |
| DD (1) | DD114072A5 (xx) |
| DE (1) | DE2446317A1 (xx) |
| DK (1) | DK506474A (xx) |
| ES (1) | ES430394A1 (xx) |
| FR (1) | FR2245361B1 (xx) |
| GB (1) | GB1474907A (xx) |
| HU (1) | HU170007B (xx) |
| NL (1) | NL7412868A (xx) |
| NO (1) | NO743281L (xx) |
| SE (1) | SE389108B (xx) |
| SU (1) | SU544370A3 (xx) |
| ZA (1) | ZA745927B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182729A (en) * | 1972-06-22 | 1980-01-08 | Sterling Drug Inc. | Arylvinyl cyclopropyl ketones |
| US4206230A (en) * | 1978-11-13 | 1980-06-03 | Mobil Oil Corporation | Phenyl cyclopropyl ketone insecticides |
| AU2002326806B2 (en) * | 2001-08-29 | 2007-07-19 | Endo Pharmaceuticals, Inc. | Analgetic pyrroline derivatives |
| US20070129434A1 (en) * | 2002-08-29 | 2007-06-07 | Richard Smith-Carliss | Analgesics and methods of use |
| US20060074083A1 (en) * | 2004-10-05 | 2006-04-06 | Merz Pharma Gmbh & Co. Kgaa | Cyclic and acyclic propenones for treating CNS disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135766A (en) * | 1961-10-03 | 1964-06-02 | Mead Johnson & Co | 3-substituted-3-pyrrolidinols |
| US3452015A (en) * | 1967-07-12 | 1969-06-24 | Lilly Co Eli | Synthesis of beta,beta-alkyl pyrrolidines |
-
1973
- 1973-09-27 GB GB4539573A patent/GB1474907A/en not_active Expired
-
1974
- 1974-09-02 FR FR7429834A patent/FR2245361B1/fr not_active Expired
- 1974-09-04 CA CA208,497A patent/CA1025456A/en not_active Expired
- 1974-09-11 US US05/505,084 patent/US4005103A/en not_active Expired - Lifetime
- 1974-09-11 CS CS746256A patent/CS188203B2/cs unknown
- 1974-09-12 NO NO743281A patent/NO743281L/no unknown
- 1974-09-18 CH CH1267574A patent/CH593255A5/xx not_active IP Right Cessation
- 1974-09-18 ZA ZA00745927A patent/ZA745927B/xx unknown
- 1974-09-24 AT AT765574A patent/AT336601B/de not_active IP Right Cessation
- 1974-09-24 AR AR255723A patent/AR209281A1/es active
- 1974-09-25 ES ES430394A patent/ES430394A1/es not_active Expired
- 1974-09-26 SE SE7412161A patent/SE389108B/xx unknown
- 1974-09-26 DK DK506474A patent/DK506474A/da unknown
- 1974-09-26 DD DD181351A patent/DD114072A5/xx unknown
- 1974-09-26 SU SU2063054A patent/SU544370A3/ru active
- 1974-09-26 HU HUHE664A patent/HU170007B/hu unknown
- 1974-09-27 JP JP49112245A patent/JPS5076052A/ja active Pending
- 1974-09-27 NL NL7412868A patent/NL7412868A/xx not_active Application Discontinuation
- 1974-09-27 DE DE19742446317 patent/DE2446317A1/de active Pending
-
1975
- 1975-01-16 BE BE2053875A patent/BE820191A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE389108B (sv) | 1976-10-25 |
| DD114072A5 (xx) | 1975-07-12 |
| CA1025456A (en) | 1978-01-31 |
| FR2245361A1 (xx) | 1975-04-25 |
| DE2446317A1 (de) | 1975-04-10 |
| AU7332474A (en) | 1976-03-18 |
| JPS5076052A (xx) | 1975-06-21 |
| ES430394A1 (es) | 1976-10-16 |
| SE7412161L (xx) | 1975-04-01 |
| SU544370A3 (ru) | 1977-01-25 |
| ATA765574A (de) | 1976-09-15 |
| DK506474A (xx) | 1975-06-02 |
| ZA745927B (en) | 1975-10-29 |
| AR209281A1 (es) | 1977-04-15 |
| GB1474907A (en) | 1977-05-25 |
| NL7412868A (nl) | 1975-04-02 |
| CH593255A5 (xx) | 1977-11-30 |
| US4005103A (en) | 1977-01-25 |
| CS188203B2 (en) | 1979-02-28 |
| HU170007B (xx) | 1977-03-28 |
| BE820191A (fr) | 1975-01-16 |
| FR2245361B1 (xx) | 1977-11-04 |
| AT336601B (de) | 1977-05-10 |
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