DE2042750A1 - Neue basisch substituierte ter tiare Butanole - Google Patents
Neue basisch substituierte ter tiare ButanoleInfo
- Publication number
- DE2042750A1 DE2042750A1 DE19702042750 DE2042750A DE2042750A1 DE 2042750 A1 DE2042750 A1 DE 2042750A1 DE 19702042750 DE19702042750 DE 19702042750 DE 2042750 A DE2042750 A DE 2042750A DE 2042750 A1 DE2042750 A1 DE 2042750A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- propyl
- benzyl alcohol
- amino
- general formula
- 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- CHRAJVQLWOMYQI-SCZZXKLOSA-N (1s,5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical group C1NC[C@H]2CC[C@]1(C)C2(C)C CHRAJVQLWOMYQI-SCZZXKLOSA-N 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- KURZCZMGELAPSV-UHFFFAOYSA-N [Br].[I] Chemical compound [Br].[I] KURZCZMGELAPSV-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000006196 deacetylation Effects 0.000 claims 1
- 238000003381 deacetylation reaction Methods 0.000 claims 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- -1 hydroxy- Chemical class 0.000 abstract description 85
- 230000000694 effects Effects 0.000 abstract description 5
- 208000025865 Ulcer Diseases 0.000 abstract description 4
- 230000003474 anti-emetic effect Effects 0.000 abstract description 4
- 239000002111 antiemetic agent Substances 0.000 abstract description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 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 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 120
- 238000002844 melting Methods 0.000 description 58
- 230000008018 melting Effects 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 235000019445 benzyl alcohol Nutrition 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 description 2
- 230000002964 excitative effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 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
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07D295/088—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 to an acyclic saturated chain
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (41)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE757408D BE757408A (fr) | 1969-10-13 | Nouveaux butanols tertiaires a constituants basiques | |
| DE19702042750 DE2042750A1 (de) | 1970-08-28 | 1970-08-28 | Neue basisch substituierte ter tiare Butanole |
| SU1691950A SU421179A3 (enExample) | 1970-08-28 | 1970-09-29 | |
| SU1691523A SU420170A3 (enExample) | 1970-08-28 | 1970-09-29 | |
| BG017131A BG17748A3 (bg) | 1970-08-28 | 1970-10-02 | Метод за получаване на нови базично субституирани третични бутаноли |
| BG015777A BG17504A3 (bg) | 1969-10-13 | 1970-10-02 | Метод за получаване на нови базично субституиране терциерни бутаноли |
| BG017130A BG17747A3 (bg) | 1970-08-28 | 1970-10-02 | Метод за получаване на базично субституирани третични бутаноли |
| ES384182A ES384182A1 (es) | 1969-10-13 | 1970-10-02 | Procedimiento para la preparacion de nuevos butanoles ter- ciarios basicamente sustituidos. |
| CS788*[A CS168544B2 (enExample) | 1970-08-28 | 1970-10-06 | |
| CS787*[A CS168543B2 (enExample) | 1970-08-28 | 1970-10-06 | |
| CH1342073A CH563337A5 (enExample) | 1969-10-13 | 1970-10-08 | |
| CH1342173A CH550137A (de) | 1969-10-13 | 1970-10-08 | Verfahren zur herstellung neuer basisch substituierter tertiaerer butanole. |
| CH1493470A CH550769A (de) | 1969-10-13 | 1970-10-08 | Verfahren zur herstellung neuer basisch substituierter tertiaerer butanole. |
| CH1342273A CH550138A (de) | 1969-10-13 | 1970-10-08 | Verfahren zur herstellung neuer basisch substituierter tertiaerer butanole. |
| NL7014910A NL7014910A (enExample) | 1969-10-13 | 1970-10-12 | |
| YU2507/70A YU33719B (en) | 1969-10-13 | 1970-10-12 | Process for preparing novel basic-substituted tertiary butanols |
| US00080226A US3794645A (en) | 1969-10-13 | 1970-10-12 | 1-(m-halo-p-amino-phenyl)-4-aminotert.butanols-(1)and salts thereof |
| JP45089592A JPS5033047B1 (enExample) | 1969-10-13 | 1970-10-12 | |
| FI2758/70A FI52973C (enExample) | 1969-10-13 | 1970-10-12 | |
| KR7001422A KR780000213B1 (en) | 1970-08-28 | 1970-10-12 | Process for producting basically substitued tertiary butanols |
| DK516970AA DK136151B (da) | 1969-10-13 | 1970-10-12 | Analogifremgangsmåde til fremstilling af basisk substituerede tertiære butanoler eller syreadditionssalte deraf. |
| PL1970174654A PL84543B1 (enExample) | 1970-08-28 | 1970-10-12 | |
| IL35434A IL35434A (en) | 1969-10-13 | 1970-10-12 | Basically substituted tertiary butanols,their preparation and pharmaceutical compositions containing them |
| GB4839970A GB1318901A (en) | 1969-10-13 | 1970-10-12 | Alpha-aminoalkylbenzyl alcohols |
| NO03826/70A NO130155B (enExample) | 1969-10-13 | 1970-10-12 | |
| RO6702670A RO58298A (enExample) | 1969-10-13 | 1970-10-13 | |
| RO67024A RO59184A (enExample) | 1970-08-28 | 1970-10-13 | |
| FR707036907A FR2070122B1 (enExample) | 1969-10-13 | 1970-10-13 | |
| RO64671A RO56876A (enExample) | 1969-10-13 | 1970-10-13 | |
| SE7013843A SE372932B (enExample) | 1969-10-13 | 1970-10-13 | |
| AT312572A AT308074B (de) | 1970-08-28 | 1970-10-13 | Verfahren zur Herstellung von neuen substituierten 1-(4'-Amino-3'-halogenphenyl)-4-aminobutan-(1)-olen und deren Säureadditionssalzen |
| IE1315/70A IE34663B1 (en) | 1969-10-13 | 1970-10-13 | Novel alpha-aminoalkylbenzyl alcohols |
| AT312372A AT308073B (de) | 1970-08-28 | 1970-10-13 | Verfahren zur Herstellung von neuen substituierten 1-(4'-Amino-3'-halogenphenyl)-4-aminobutan-(1)-olen und deren Säureadditionssalzen |
| RO67025A RO58297A (enExample) | 1970-08-28 | 1970-10-13 | |
| AT312472A AT310723B (de) | 1970-08-28 | 1970-10-13 | Verfahren zur Herstellung von neuen substituierten 1-(4'-Amino-3'-halogenphenyl)-4-aminobutan-(1)-olen und deren Säureadditionssalzen |
| ES385472A ES385472A1 (es) | 1970-08-28 | 1970-11-12 | Procedimiento para la preparacion de nuevos butanoles ter- ciarios basicamente sustituidos. |
| ES385473A ES385473A1 (es) | 1970-08-28 | 1970-11-12 | Procedimiento para la preparacion de nuevos butanoles ter- ciarios basicamente sustituidos. |
| ES385471A ES385471A1 (es) | 1970-08-28 | 1970-11-12 | Procedimiento para la preparacion de nuevos butanoles ter- ciarios basicamente sustituidos. |
| KR7800223A KR780000251B1 (en) | 1970-08-28 | 1978-01-28 | Process for preparation of basically substituded tertiary butanols |
| KR7800224A KR780000230B1 (en) | 1970-08-28 | 1978-01-28 | Process for preparation of basically substituted tertiary butanols |
| KR7800222A KR780000250B1 (en) | 1970-08-28 | 1978-01-28 | Process for preparation of basically substituted tertiary tbutanols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702042750 DE2042750A1 (de) | 1970-08-28 | 1970-08-28 | Neue basisch substituierte ter tiare Butanole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2042750A1 true DE2042750A1 (de) | 1972-03-02 |
Family
ID=5780991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702042750 Pending DE2042750A1 (de) | 1969-10-13 | 1970-08-28 | Neue basisch substituierte ter tiare Butanole |
Country Status (9)
| Country | Link |
|---|---|
| KR (2) | KR780000213B1 (enExample) |
| AT (3) | AT308074B (enExample) |
| BG (2) | BG17748A3 (enExample) |
| CS (2) | CS168543B2 (enExample) |
| DE (1) | DE2042750A1 (enExample) |
| ES (3) | ES385471A1 (enExample) |
| PL (1) | PL84543B1 (enExample) |
| RO (2) | RO59184A (enExample) |
| SU (2) | SU421179A3 (enExample) |
-
1970
- 1970-08-28 DE DE19702042750 patent/DE2042750A1/de active Pending
- 1970-09-29 SU SU1691950A patent/SU421179A3/ru active
- 1970-09-29 SU SU1691523A patent/SU420170A3/ru active
- 1970-10-02 BG BG017131A patent/BG17748A3/xx unknown
- 1970-10-02 BG BG017130A patent/BG17747A3/xx unknown
- 1970-10-06 CS CS787*[A patent/CS168543B2/cs unknown
- 1970-10-06 CS CS788*[A patent/CS168544B2/cs unknown
- 1970-10-12 KR KR7001422A patent/KR780000213B1/ko not_active Expired
- 1970-10-12 PL PL1970174654A patent/PL84543B1/pl unknown
- 1970-10-13 RO RO67024A patent/RO59184A/ro unknown
- 1970-10-13 RO RO67025A patent/RO58297A/ro unknown
- 1970-10-13 AT AT312572A patent/AT308074B/de active
- 1970-10-13 AT AT312372A patent/AT308073B/de not_active IP Right Cessation
- 1970-10-13 AT AT312472A patent/AT310723B/de not_active IP Right Cessation
- 1970-11-12 ES ES385471A patent/ES385471A1/es not_active Expired
- 1970-11-12 ES ES385473A patent/ES385473A1/es not_active Expired
- 1970-11-12 ES ES385472A patent/ES385472A1/es not_active Expired
-
1978
- 1978-01-28 KR KR7800224A patent/KR780000230B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS168543B2 (enExample) | 1976-06-29 |
| BG17748A3 (bg) | 1973-12-25 |
| ES385472A1 (es) | 1973-05-01 |
| ES385471A1 (es) | 1973-05-01 |
| RO59184A (enExample) | 1976-02-15 |
| SU420170A3 (enExample) | 1974-03-15 |
| ES385473A1 (es) | 1973-05-01 |
| PL84543B1 (enExample) | 1976-04-30 |
| RO58297A (enExample) | 1975-07-15 |
| BG17747A3 (bg) | 1973-12-25 |
| AT308074B (de) | 1973-06-25 |
| AT310723B (de) | 1973-10-10 |
| KR780000230B1 (en) | 1978-07-01 |
| CS168544B2 (enExample) | 1976-06-29 |
| SU421179A3 (enExample) | 1974-03-25 |
| KR780000213B1 (en) | 1978-06-12 |
| AT308073B (de) | 1973-06-25 |
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