CH421078A - Verfahren zur Herstellung von Aminoacetylenverbindungen - Google Patents
Verfahren zur Herstellung von AminoacetylenverbindungenInfo
- Publication number
- CH421078A CH421078A CH856161A CH856161A CH421078A CH 421078 A CH421078 A CH 421078A CH 856161 A CH856161 A CH 856161A CH 856161 A CH856161 A CH 856161A CH 421078 A CH421078 A CH 421078A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- formula
- compound
- hydrogen atom
- halogen atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical group NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 dialkylamino radical Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical class CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- FKAADILEVMMDFV-UHFFFAOYSA-N 1-aminobut-2-yn-1-ol Chemical compound CC#CC(N)O FKAADILEVMMDFV-UHFFFAOYSA-N 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000000155 melt Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 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 7
- IRAVYHIRJICKRS-UHFFFAOYSA-N acetic acid;hypochlorous acid Chemical compound ClO.CC(O)=O IRAVYHIRJICKRS-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RPUJAOFSZSEVPC-UHFFFAOYSA-N 4-chlorobut-2-yn-1-ol Chemical compound OCC#CCCl RPUJAOFSZSEVPC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- AYHZMFINEQYCPE-UHFFFAOYSA-N methyl 2-(2,2-diphenylethoxy)acetate Chemical compound C=1C=CC=CC=1C(COCC(=O)OC)C1=CC=CC=C1 AYHZMFINEQYCPE-UHFFFAOYSA-N 0.000 description 2
- SPTZOODMHSABLY-UHFFFAOYSA-N methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OC)C1CCCCC1 SPTZOODMHSABLY-UHFFFAOYSA-N 0.000 description 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 1
- AEIGUJIDYBREEB-UHFFFAOYSA-N 2-hydroxy-2-(2-methylphenyl)-2-phenylacetic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C1=CC=CC=C1 AEIGUJIDYBREEB-UHFFFAOYSA-N 0.000 description 1
- QKKIKZSTHNAFNR-UHFFFAOYSA-N 3-aminobut-1-yn-1-ol Chemical class CC(N)C#CO QKKIKZSTHNAFNR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WEJAUBZMWTYYNI-UHFFFAOYSA-N CC(Cc1ccccc1)(C(Cl)=O)c1ccccc1 Chemical compound CC(Cc1ccccc1)(C(Cl)=O)c1ccccc1 WEJAUBZMWTYYNI-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BSKZDJXVMPWPRA-UHFFFAOYSA-N O.[Br] Chemical class O.[Br] BSKZDJXVMPWPRA-UHFFFAOYSA-N 0.000 description 1
- OOEWZEXEJQEFJO-UHFFFAOYSA-N O.[I] Chemical class O.[I] OOEWZEXEJQEFJO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- YTRNSQPXEDGWMR-UHFFFAOYSA-N alpha-Cyclohexylmandelic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 YTRNSQPXEDGWMR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FDOMEEULKNYULF-UHFFFAOYSA-N heptane;methanol Chemical compound OC.CCCCCCC FDOMEEULKNYULF-UHFFFAOYSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LQPRNRFJJUSONA-UHFFFAOYSA-N methyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OC)C1=CC=CC=C1 LQPRNRFJJUSONA-UHFFFAOYSA-N 0.000 description 1
- LJFIHTFNTGQZJL-UHFFFAOYSA-N methyl 2-hydroxy-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OC)C1=CC=CC=C1 LJFIHTFNTGQZJL-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4529260A | 1960-07-26 | 1960-07-26 | |
| US118261A US3176019A (en) | 1960-07-26 | 1961-06-20 | Substituted aminobutynyl acetates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH421078A true CH421078A (de) | 1966-09-30 |
Family
ID=26722613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH856161A CH421078A (de) | 1960-07-26 | 1961-07-20 | Verfahren zur Herstellung von Aminoacetylenverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3176019A (enExample) |
| BE (1) | BE606560A (enExample) |
| CH (1) | CH421078A (enExample) |
| DE (1) | DE1216866B (enExample) |
| DK (1) | DK113854B (enExample) |
| ES (1) | ES269353A1 (enExample) |
| FR (1) | FR1325M (enExample) |
| GB (1) | GB940540A (enExample) |
| NL (2) | NL267508A (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5736577A (en) * | 1995-01-31 | 1998-04-07 | Sepracor, Inc. | Methods and compositions for treating urinary incontinence using optically pure (S)-oxybutynin |
| US3864388A (en) * | 1970-12-29 | 1975-02-04 | Sumitomo Chemical Co | Alkynyl esters of {60 -alkoxy-{60 -phenyl alkenoic acid |
| US5036107A (en) * | 1986-06-27 | 1991-07-30 | Marion Merrell Dow Inc. | 1,7-substituted heptyn-2-ones and use |
| US4957941A (en) * | 1987-11-16 | 1990-09-18 | United Pharmaceuticals, Inc. | Anti-spasmdoic agents having an acetylenic bond |
| IL91377A (en) * | 1988-09-14 | 1996-09-12 | Nippon Shinyaku Co Ltd | Derivatives of botinylamine glycolate |
| US5677346A (en) * | 1995-01-31 | 1997-10-14 | Sepracor, Inc. | Treating urinary incontinence using (S)-desethyloxybutynin |
| US5532278A (en) * | 1995-01-31 | 1996-07-02 | Sepracor, Inc. | Methods and compositions for treating urinary incontinence using optically pure (S)-oxybutynin |
| AU3799997A (en) * | 1996-07-09 | 1998-02-02 | Sepracor, Inc. | Dextrorotatory isomers of oxybutynin and desethyloxybutynin in the treatment of gastrointestinal hyperactivity |
| US6140529A (en) * | 1998-10-22 | 2000-10-31 | Sepracor Inc. | Synthesis of optically active cyclohexylphenylglycolate esters |
| US5973182A (en) * | 1998-10-22 | 1999-10-26 | Sepracor Inc. | Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters |
| AU5378201A (en) * | 2000-04-26 | 2001-11-07 | Watson Pharmaceuticals Inc | Minimizing adverse experience associated with oxybutynin therapy |
| US7179483B2 (en) | 2000-04-26 | 2007-02-20 | Watson Pharmaceuticals, Inc. | Compositions and methods for transdermal oxybutynin therapy |
| US6890920B2 (en) | 2001-10-26 | 2005-05-10 | Pharmacia & Upjohn Company | Quaternary ammonium compounds |
| EA200500173A1 (ru) | 2002-07-08 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные 3,6-дизамещенного азабицикло[3.1.0]гексана в качестве антагонистов мускариновых рецепторов |
| EP1546098B1 (en) * | 2002-07-31 | 2008-05-28 | Ranbaxy Laboratories Limited | 3,6-disubstituted azabicyclo [3.1.0]hexane derivatives useful as muscarinic receptor antagonists |
| HK1079708A1 (zh) * | 2002-08-09 | 2006-04-13 | Ranbaxy Laboratories, Ltd. | 可用作毒蕈碱性受体拮抗剂的3，6-二取代氮杂二环[3．1．10]己烷衍生物 |
| EP1534675B1 (en) * | 2002-08-23 | 2009-02-25 | Ranbaxy Laboratories, Ltd. | Fluoro and sulphonylamino containing 3,6-disubstituted azabicyclo¬3.1.0 hexane derivatives as muscarinic receptor antagonists |
| TW200412945A (en) | 2002-10-25 | 2004-08-01 | Upjohn Co | Quaternary ammonium compounds |
| AU2002353286A1 (en) | 2002-12-10 | 2004-06-30 | Ranbaxy Laboratories Limited | 3,6-disubstituted azabicyclo (3.1.0) hexane derivatives as muscarinic receptor antagonists |
| WO2004056767A1 (en) * | 2002-12-23 | 2004-07-08 | Ranbaxy Laboratories Limited | 1-substituted-3-pyrrolidine derivatives as muscarinic receptor antagonists |
| AU2002347553A1 (en) * | 2002-12-23 | 2004-07-14 | Ranbaxy Laboratories Limited | Flavaxate derivatives as muscarinic receptor antagonists |
| US7488748B2 (en) | 2003-01-28 | 2009-02-10 | Ranbaxy Laboratories Limited | 3,6-Disubstituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| EP1618091A1 (en) * | 2003-04-09 | 2006-01-25 | Ranbaxy Laboratories, Ltd. | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| EP1615634B1 (en) * | 2003-04-10 | 2007-05-16 | Ranbaxy Laboratories, Ltd. | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| WO2004089899A1 (en) | 2003-04-10 | 2004-10-21 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| WO2004089900A1 (en) * | 2003-04-11 | 2004-10-21 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| DE602004018844D1 (de) * | 2004-06-16 | 2009-02-12 | Ranbaxy Lab Ltd | Als antagonisten des muscarinrezeptors geeignete xanthinderivate |
| EP1781607A2 (en) * | 2004-08-19 | 2007-05-09 | Ranbaxy Laboratories Limited | Pyrrolidine derivatives as muscarinic receptor antagonists |
| US20080280883A1 (en) * | 2004-09-24 | 2008-11-13 | Mohammad Salman | Muscarinic Receptor Antagonists |
| WO2006035303A1 (en) * | 2004-09-29 | 2006-04-06 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| WO2006054162A1 (en) * | 2004-11-19 | 2006-05-26 | Ranbaxy Laboratories Limited | Azabicyclic muscarinic receptor antagonists |
| EP1828126A1 (en) * | 2004-12-15 | 2007-09-05 | Ranbaxy Laboratories Limited | Acid addition salts of muscarinic receptor antagonists |
| US20080319043A1 (en) * | 2005-05-03 | 2008-12-25 | Mohammad Salman | 3,6-Disubstituted Azabicyclo (3.1.0) Hexane Derivatives as Muscarinic Receptor Antagonists |
| WO2007045979A1 (en) | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of muscarinic receptor antagonists |
| US20090010923A1 (en) * | 2007-04-24 | 2009-01-08 | University Of Maryland, Baltimore | Treatment of cancer with anti-muscarinic receptor agents |
| US20110087042A1 (en) * | 2008-02-04 | 2011-04-14 | Matrix Laboratories Limited | Crystalline oxybutynin and process for preparing the same |
| CA2796877A1 (en) | 2010-04-30 | 2011-11-03 | Merck Sharp & Dohme Corp. | Novel beta 3 adrenergic receptor agonists |
| PE20131341A1 (es) | 2010-08-03 | 2013-12-07 | Altherx Inc | Combinaciones de agonistas del receptor beta-3-adrenergico y antagonistas del receptor muscarinico para tratar vejiga hiperactiva |
| US9907767B2 (en) | 2010-08-03 | 2018-03-06 | Velicept Therapeutics, Inc. | Pharmaceutical compositions and the treatment of overactive bladder |
| TW201338772A (zh) | 2012-02-09 | 2013-10-01 | Altherx Inc | 藥學組合物 |
| MX2017007054A (es) | 2014-12-03 | 2018-05-02 | Velicept Therapeutics Inc | Composiciones y métodos para usar solabegron de liberación modificada para sintomas del tracto urinario inferior. |
| CN108290824B (zh) | 2015-10-23 | 2022-03-11 | B3Ar治疗股份有限公司 | 索拉贝隆两性离子及其应用 |
| CN111670050A (zh) | 2018-01-30 | 2020-09-15 | 爱普宁公司(特拉华) | 用于治疗睡眠呼吸暂停的方法和组合物 |
| EP4146621A1 (en) | 2020-05-05 | 2023-03-15 | Apnimed, Inc. (Delaware) | Polymorphic forms of (r)-oxybutynin hydrochloride |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE895595C (de) * | 1943-09-29 | 1953-11-05 | Basf Ag | Verfahren zur Herstellung von Aminoalkinolen |
| DE1003209B (de) * | 1953-03-24 | 1957-02-28 | Basf Ag | Verfahren zur Herstellung spasmolytisch wirksamer basischer Carbinole |
| US2867619A (en) * | 1956-11-05 | 1959-01-06 | Lakeside Lab Inc | Aminoalkynyl-n-alkylpiperidine carboxylates |
| DE1083254B (de) * | 1957-04-01 | 1960-06-15 | Lakeside Lab In | Verfahren zur Herstellung von blutdrucksenkenden N-disubstituierten Diaminoalkinen, deren Saeureadditionssalzen oder quaternaeren Ammoniumsalzen |
| DE1100617B (de) * | 1959-10-22 | 1961-03-02 | Basf Ag | Verfahren zur Herstellung von 1-Dialkylamino-4-hydroxy-acetylenen-(2) |
-
0
- NL NL124473D patent/NL124473C/xx active
- NL NL267508D patent/NL267508A/xx unknown
-
1961
- 1961-06-20 US US118261A patent/US3176019A/en not_active Expired - Lifetime
- 1961-07-19 DE DEM49737A patent/DE1216866B/de active Pending
- 1961-07-20 CH CH856161A patent/CH421078A/de unknown
- 1961-07-20 FR FR868440A patent/FR1325M/fr active Active
- 1961-07-24 ES ES0269353A patent/ES269353A1/es not_active Expired
- 1961-07-25 DK DK304861AA patent/DK113854B/da unknown
- 1961-07-25 GB GB26864/61A patent/GB940540A/en not_active Expired
- 1961-07-26 BE BE606560A patent/BE606560A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES269353A1 (es) | 1961-11-16 |
| NL267508A (enExample) | |
| DK113854B (da) | 1969-05-05 |
| GB940540A (en) | 1963-10-30 |
| DE1216866B (de) | 1966-05-18 |
| NL124473C (enExample) | |
| FR1325M (fr) | 1962-05-21 |
| BE606560A (fr) | 1962-01-26 |
| US3176019A (en) | 1965-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1216866B (de) | Verfahren zur Herstellung von Carbonsaeureestern des 4-Aminobutin-(2)-ols-(1) und deren therapeutisch vertraeglichen Salzen | |
| DE1543715A1 (de) | Verfahren zur Herstellung von basischen Derivaten von Phthalanen und Isochromanen | |
| DE2503002A1 (de) | Substituierte piperidinderivate, ein verfahren zu ihrer herstellung sowie arzneimittel | |
| CH633249A5 (de) | Verfahren zur herstellung von neuen polyprenylderivaten. | |
| CH639086A5 (de) | Verfahren zur herstellung von piperidinopropanolderivaten. | |
| DE949105C (de) | Verfahren zur Herstellung von neuen, fungiciden und protozoociden aromatischen Aminoketonen und deren Salzen | |
| AT338257B (de) | Verfahren zur herstellung von neuen naphthalinderivaten | |
| DE2616484C3 (de) | Basische Benzoyläther, deren Salze und quartäre Ammoniumverbindungen sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE2819896A1 (de) | Chromenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2412520A1 (de) | Tricyclische verbindungen | |
| AT242137B (de) | Verfahren zur Herstellung von neuen Derivaten des 4-Aminobutin-(2, 3)-ols-1 und deren Salzen | |
| DE2560602C2 (de) | Sauerstoffhaltige Diarylamidine | |
| DE2155406B2 (de) | 3- eckige Klammer auf 2-(3-Bromphenyl)-5-tetrazolyl eckige Klammer zu -propionsäureamide | |
| CH356121A (de) | Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren | |
| DE2508331A1 (de) | 1-(3-phenylpropyl)-4-furoylpiperazine | |
| AT333265B (de) | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze | |
| US3127407A (en) | Certain 1-(chlorophenyl)-2-tertiary amino alkanes | |
| AT254867B (de) | Verfahren zur Herstellung von neuen 3,5-disubstituierten Isoxazol-Derivaten | |
| AT231439B (de) | Verfahren zur Herstellung von neuen o-Alkoxybenzoesäureaminoalkylamiden | |
| DE2302000C3 (de) | 2-Hydroxy-2-phenylathylamine, deren Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneipräparate | |
| AT223601B (de) | Verfahren zur Herstellung neuer o- und p-(β-Dialkylaminoäthoxyphenyl)-ketone und deren salzartiger Abkömmlinge | |
| CH621549A5 (enExample) | ||
| AT238207B (de) | Verfahren zur Herstellung von neuen asymmetrisch substituierten Piperazinderivaten | |
| AT334350B (de) | Verfahren zur herstellung von neuen 3- (4-biphenylyl) -buttersauren, deren estern, amiden und salzen | |
| AT284828B (de) | Verfahren zur Herstellung von neuen N-substituierten 2-Phenyl-2-(2'-hydroxy-1'-naphthyl)-äthylaminen und deren Säureadditionssalzen |