DE1793640B1 - 1-(p-chlorphenyl)-2-phenyl-2-propionyloxy-3-(dimethylaminomethyl)-3-buten und seine salze sowie verfahren zu ihrer herstellung - Google Patents
1-(p-chlorphenyl)-2-phenyl-2-propionyloxy-3-(dimethylaminomethyl)-3-buten und seine salze sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE1793640B1 DE1793640B1 DE19661793640 DE1793640A DE1793640B1 DE 1793640 B1 DE1793640 B1 DE 1793640B1 DE 19661793640 DE19661793640 DE 19661793640 DE 1793640 A DE1793640 A DE 1793640A DE 1793640 B1 DE1793640 B1 DE 1793640B1
- Authority
- DE
- Germany
- Prior art keywords
- salts
- phenyl
- dimethylaminomethyl
- chlorophenyl
- propionyloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 5
- MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical compound OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 title 1
- -1 1- (p-Chlorophenyl) -2-phenyl-2-propionyloxy-3- (dimethylaminomethyl) -3-butene Chemical compound 0.000 claims description 12
- GUXXMLZIXGCSQC-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[(dimethylamino)methyl]-2-phenylbut-3-en-2-ol Chemical compound ClC1=CC=C(C=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 GUXXMLZIXGCSQC-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 230000000202 analgesic effect Effects 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 238000003747 Grignard reaction Methods 0.000 claims 2
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 231100001274 therapeutic index Toxicity 0.000 claims 2
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 claims 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 claims 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 1
- 241000282472 Canis lupus familiaris Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 244000248349 Citrus limon Species 0.000 claims 1
- 235000005979 Citrus limon Nutrition 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 241000257303 Hymenoptera Species 0.000 claims 1
- 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 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 235000011430 Malus pumila Nutrition 0.000 claims 1
- 235000015103 Malus silvestris Nutrition 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 241000283973 Oryctolagus cuniculus Species 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229960004909 aminosalicylic acid Drugs 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229940124584 antitussives Drugs 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 150000002561 ketenes Chemical class 0.000 claims 1
- 229940040102 levulinic acid Drugs 0.000 claims 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical class [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 230000006289 propionylation Effects 0.000 claims 1
- 238000010515 propionylation reaction Methods 0.000 claims 1
- 229940107700 pyruvic acid Drugs 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 230000002048 spasmolytic effect Effects 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims 1
- 235000014101 wine Nutrition 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-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
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- NLOUUOHFCQJOCA-UHFFFAOYSA-N bis(2-benzyl-4-chlorophenyl)methanone Chemical compound C=1C=CC=CC=1CC1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1CC1=CC=CC=C1 NLOUUOHFCQJOCA-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000000699 topical effect Effects 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
- C07D295/092—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 with aromatic radicals attached to the chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Remote Monitoring And Control Of Power-Distribution Networks (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267765A CH465584A (de) | 1965-02-26 | 1965-02-26 | Verfahren zur Herstellung von neuen tertiären Aminen |
| CH902865 | 1965-06-28 | ||
| CH1311165 | 1965-09-22 | ||
| CH1811965 | 1965-12-30 | ||
| CH1811865 | 1965-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793640B1 true DE1793640B1 (de) | 1973-04-26 |
Family
ID=27509073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568254 Pending DE1568254A1 (de) | 1965-02-26 | 1966-02-17 | Neue ungesaettigte tertiaere Amine |
| DE19661793640 Pending DE1793640B1 (de) | 1965-02-26 | 1966-02-17 | 1-(p-chlorphenyl)-2-phenyl-2-propionyloxy-3-(dimethylaminomethyl)-3-buten und seine salze sowie verfahren zu ihrer herstellung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568254 Pending DE1568254A1 (de) | 1965-02-26 | 1966-02-17 | Neue ungesaettigte tertiaere Amine |
Country Status (16)
| Country | Link |
|---|---|
| BE (3) | BE677035A (cs) |
| BR (3) | BR6677344D0 (cs) |
| CH (2) | CH465584A (cs) |
| CY (1) | CY556A (cs) |
| DE (2) | DE1568254A1 (cs) |
| DK (3) | DK123023B (cs) |
| FI (1) | FI44601C (cs) |
| FR (4) | FR1468478A (cs) |
| GB (3) | GB1117623A (cs) |
| IL (1) | IL25127A (cs) |
| LU (1) | LU50473A1 (cs) |
| MY (1) | MY7000162A (cs) |
| NL (3) | NL6602536A (cs) |
| NO (1) | NO115389B (cs) |
| SE (3) | SE348724B (cs) |
| SU (1) | SU372806A3 (cs) |
-
1965
- 1965-02-26 CH CH267765A patent/CH465584A/de unknown
- 1965-02-26 CH CH1401167A patent/CH475190A/de not_active IP Right Cessation
-
1966
- 1966-02-07 IL IL2512766A patent/IL25127A/xx unknown
- 1966-02-08 GB GB547366A patent/GB1117623A/en not_active Expired
- 1966-02-08 GB GB547266A patent/GB1117622A/en not_active Expired
- 1966-02-08 GB GB547166A patent/GB1068497A/en not_active Expired
- 1966-02-16 LU LU50473A patent/LU50473A1/xx unknown
- 1966-02-17 FR FR50038A patent/FR1468478A/fr not_active Expired
- 1966-02-17 DE DE19661568254 patent/DE1568254A1/de active Pending
- 1966-02-17 DE DE19661793640 patent/DE1793640B1/de active Pending
- 1966-02-17 FR FR50039A patent/FR1468479A/fr not_active Expired
- 1966-02-23 FI FI44866A patent/FI44601C/fi active
- 1966-02-24 BR BR17734466A patent/BR6677344D0/pt unknown
- 1966-02-24 BR BR17733766A patent/BR6677337D0/pt unknown
- 1966-02-24 BR BR17733666A patent/BR6677336D0/pt unknown
- 1966-02-25 SE SE246666A patent/SE348724B/xx unknown
- 1966-02-25 NL NL6602536A patent/NL6602536A/xx unknown
- 1966-02-25 SE SE246566A patent/SE325266B/xx unknown
- 1966-02-25 DK DK98666A patent/DK123023B/da unknown
- 1966-02-25 SE SE246766A patent/SE348454B/xx unknown
- 1966-02-25 BE BE677035D patent/BE677035A/xx unknown
- 1966-02-25 DK DK98766A patent/DK122878B/da unknown
- 1966-02-25 NO NO16185366A patent/NO115389B/no unknown
- 1966-02-25 BE BE677034D patent/BE677034A/xx unknown
- 1966-02-25 DK DK98566A patent/DK118601B/da unknown
- 1966-02-25 NL NL6602537A patent/NL6602537A/xx unknown
- 1966-02-25 NL NL6602535A patent/NL6602535A/xx unknown
- 1966-02-25 BE BE677036D patent/BE677036A/xx unknown
- 1966-03-29 SU SU1064790A patent/SU372806A3/ru active
- 1966-05-10 FR FR60915A patent/FR5349M/fr not_active Expired
- 1966-05-10 FR FR60914A patent/FR5348M/fr not_active Expired
-
1970
- 1970-08-19 CY CY55670A patent/CY556A/xx unknown
- 1970-12-31 MY MY7000162A patent/MY7000162A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK118601B (da) | 1970-09-14 |
| SE325266B (cs) | 1970-06-29 |
| DK122878B (da) | 1972-04-24 |
| FR5348M (cs) | 1967-09-04 |
| SE348454B (cs) | 1972-09-04 |
| NL6602536A (cs) | 1966-08-29 |
| LU50473A1 (cs) | 1966-04-18 |
| NL6602537A (cs) | 1966-08-29 |
| BE677035A (cs) | 1966-08-25 |
| DE1568252B2 (de) | 1973-01-04 |
| FR5349M (cs) | 1967-09-04 |
| FI44601C (fi) | 1971-12-10 |
| SU372806A3 (cs) | 1973-03-01 |
| FI44601B (cs) | 1971-08-31 |
| BR6677344D0 (pt) | 1973-09-06 |
| DE1568254A1 (de) | 1970-03-19 |
| DE1568253B1 (de) | 1971-07-29 |
| GB1117622A (en) | 1968-06-19 |
| SE348724B (cs) | 1972-09-11 |
| DE1568252A1 (de) | 1971-06-24 |
| NL6602535A (cs) | 1966-08-29 |
| DK123023B (da) | 1972-05-08 |
| BE677036A (cs) | 1966-08-25 |
| CY556A (en) | 1970-08-19 |
| MY7000162A (en) | 1970-12-31 |
| CH465584A (de) | 1968-11-30 |
| CH475190A (de) | 1969-07-15 |
| GB1117623A (en) | 1968-06-19 |
| NO115389B (cs) | 1968-09-30 |
| FR1468478A (fr) | 1967-02-03 |
| BR6677336D0 (pt) | 1973-09-20 |
| BR6677337D0 (pt) | 1973-09-06 |
| GB1068497A (en) | 1967-05-10 |
| FR1468479A (fr) | 1967-02-03 |
| IL25127A (en) | 1969-12-31 |
| BE677034A (cs) | 1966-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Publication of the examined application without previous publication of unexamined application |