DD142547A5 - Verfahren zur herstellung von als neuromuskulaere blockierungsmittel verwendbaren verbindungen - Google Patents
Verfahren zur herstellung von als neuromuskulaere blockierungsmittel verwendbaren verbindungen Download PDFInfo
- Publication number
- DD142547A5 DD142547A5 DD79210690A DD21069079A DD142547A5 DD 142547 A5 DD142547 A5 DD 142547A5 DD 79210690 A DD79210690 A DD 79210690A DD 21069079 A DD21069079 A DD 21069079A DD 142547 A5 DD142547 A5 DD 142547A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- item
- compound
- radical
- items
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 63
- 239000000842 neuromuscular blocking agent Substances 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 82
- -1 alkyl radical Chemical class 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical group OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims 8
- 239000002168 alkylating agent Substances 0.000 claims 8
- 150000004820 halides Chemical class 0.000 claims 6
- 239000012442 inert solvent Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001347 alkyl bromides Chemical class 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 150000001351 alkyl iodides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001348 alkyl chlorides Chemical class 0.000 claims 1
- DCVXWERGVUVVLH-UHFFFAOYSA-N azane;isoquinoline Chemical group N.C1=NC=CC2=CC=CC=C21 DCVXWERGVUVVLH-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000002999 depolarising effect Effects 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 230000009471 action Effects 0.000 description 14
- 238000009835 boiling Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910021607 Silver chloride Inorganic materials 0.000 description 8
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 8
- 241000282693 Cercopithecidae Species 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- KGPAYJZAMGEDIQ-UHFFFAOYSA-N laudanosine Natural products C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1C KGPAYJZAMGEDIQ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000001356 surgical procedure Methods 0.000 description 6
- KGPAYJZAMGEDIQ-KRWDZBQOSA-N Laudanosine Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1C KGPAYJZAMGEDIQ-KRWDZBQOSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 230000001376 precipitating effect Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 229910001961 silver nitrate Inorganic materials 0.000 description 5
- MLKQJVFHEUORBO-UHFFFAOYSA-M silver;methanesulfonate Chemical compound [Ag+].CS([O-])(=O)=O MLKQJVFHEUORBO-UHFFFAOYSA-M 0.000 description 5
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 4
- 206010002091 Anaesthesia Diseases 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 150000001649 bromium compounds Chemical group 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 4
- JFJZZMVDLULRGK-URLMMPGGSA-O tubocurarine Chemical compound C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 JFJZZMVDLULRGK-URLMMPGGSA-O 0.000 description 4
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
- ALQIPWOCCJXSKZ-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)C1CC1=CC(OC)=C(OC)C(OC)=C1 ALQIPWOCCJXSKZ-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 206010021118 Hypotonia Diseases 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- 241000282560 Macaca mulatta Species 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- GDMZKPQEBVBXIQ-UHFFFAOYSA-N [Ag].CC(=O)OC1=CC=C(OC(C)=O)C=C1 Chemical compound [Ag].CC(=O)OC1=CC=C(OC(C)=O)C=C1 GDMZKPQEBVBXIQ-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 239000000544 cholinesterase inhibitor Substances 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- ICLWTJIMXVISSR-UHFFFAOYSA-N gallamine Chemical compound CCN(CC)CCOC1=CC=CC(OCCN(CC)CC)=C1OCCN(CC)CC ICLWTJIMXVISSR-UHFFFAOYSA-N 0.000 description 3
- 229960003054 gallamine Drugs 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 230000036640 muscle relaxation Effects 0.000 description 3
- 230000002232 neuromuscular Effects 0.000 description 3
- GVEAYVLWDAFXET-XGHATYIMSA-N pancuronium Chemical compound C[N+]1([C@@H]2[C@@H](OC(C)=O)C[C@@H]3CC[C@H]4[C@@H]5C[C@@H]([C@@H]([C@]5(CC[C@@H]4[C@@]3(C)C2)C)OC(=O)C)[N+]2(C)CCCCC2)CCCCC1 GVEAYVLWDAFXET-XGHATYIMSA-N 0.000 description 3
- 229960005457 pancuronium Drugs 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229940032712 succinylcholine Drugs 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 3
- 229960001844 tubocurarine Drugs 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- YLCILCNDLBSOIO-UHFFFAOYSA-N (3-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(OC(=O)C=C)=C1 YLCILCNDLBSOIO-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 206010029315 Neuromuscular blockade Diseases 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- BEQWTZFUPAAWPF-UHFFFAOYSA-N [Ag].C=CC(=O)OC1=CC=C(OC(=O)C=C)C=C1 Chemical compound [Ag].C=CC(=O)OC1=CC=C(OC(=O)C=C)C=C1 BEQWTZFUPAAWPF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 2
- 229960003132 halothane Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000036543 hypotension Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FGPUFQRNZGCKQV-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC(OC)=C(OC)C(OC)=C1 FGPUFQRNZGCKQV-UHFFFAOYSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- 238000002627 tracheal intubation Methods 0.000 description 2
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 1
- WADJDQQIPSKENN-UHFFFAOYSA-N 1-methoxy-4-methylbenzene Chemical compound [CH2]C1=CC=C(OC)C=C1 WADJDQQIPSKENN-UHFFFAOYSA-N 0.000 description 1
- DDSJXCGGOXKGSJ-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC(OC)=C1OC DDSJXCGGOXKGSJ-UHFFFAOYSA-N 0.000 description 1
- KRXUBZPHAPGHPE-UHFFFAOYSA-N 3-[3-(2-carboxyethenyl)phenyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(C=CC(O)=O)=C1 KRXUBZPHAPGHPE-UHFFFAOYSA-N 0.000 description 1
- PHJVALKQCXJDNM-UHFFFAOYSA-M 6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydroisoquinolin-2-ium;iodide Chemical compound [I-].C1=2C=C(OC)C(OC)=CC=2CC[N+](C)=C1CC1=CC(OC)=C(OC)C(OC)=C1 PHJVALKQCXJDNM-UHFFFAOYSA-M 0.000 description 1
- 208000021959 Abnormal metabolism Diseases 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- BUQSONMARRFXEA-UHFFFAOYSA-N C1(=CC=C(C=C1)C=CC(=O)O)C=CC(=O)O.C(C=C)(=O)OC1=CC=C(C=C1)OC(C=C)=O.[Ag] Chemical compound C1(=CC=C(C=C1)C=CC(=O)O)C=CC(=O)O.C(C=C)(=O)OC1=CC=C(C=C1)OC(C=C)=O.[Ag] BUQSONMARRFXEA-UHFFFAOYSA-N 0.000 description 1
- CWXBDEWSZUSXBC-UHFFFAOYSA-L C1(=CC=C(C=C1)CC(=O)[O-])CC(=O)[O-].[Ag+2] Chemical compound C1(=CC=C(C=C1)CC(=O)[O-])CC(=O)[O-].[Ag+2] CWXBDEWSZUSXBC-UHFFFAOYSA-L 0.000 description 1
- 102000003914 Cholinesterases Human genes 0.000 description 1
- 108090000322 Cholinesterases Proteins 0.000 description 1
- VWLHWLSRQJQWRG-UHFFFAOYSA-O Edrophonum Chemical compound CC[N+](C)(C)C1=CC=CC(O)=C1 VWLHWLSRQJQWRG-UHFFFAOYSA-O 0.000 description 1
- 206010017999 Gastrointestinal pain Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010062530 Increased bronchial secretion Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 108010013381 Porins Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- OBSFJKTYCAXMFT-UHFFFAOYSA-N [I-].[I-].C1=CC=C2C[NH2+]CCC2=C1.C1=CC=C2C[NH2+]CCC2=C1 Chemical compound [I-].[I-].C1=CC=C2C[NH2+]CCC2=C1.C1=CC=C2C[NH2+]CCC2=C1 OBSFJKTYCAXMFT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IZTUINVRJSCOIR-UHFFFAOYSA-N benzylisoquinoline Chemical class N=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 IZTUINVRJSCOIR-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229950000405 decamethonium Drugs 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003748 edrophonium Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000006371 metabolic abnormality Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- UJJUJHTVDYXQON-UHFFFAOYSA-N nitro benzenesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C1=CC=CC=C1 UJJUJHTVDYXQON-UHFFFAOYSA-N 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940055076 parasympathomimetics choline ester Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000007925 phenylethylamine derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 102000007739 porin activity proteins Human genes 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000012232 skeletal muscle contraction Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229940120904 succinylcholine chloride Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000002465 tibial artery Anatomy 0.000 description 1
- HLXQFVXURMXRPU-UHFFFAOYSA-L trimethyl-[10-(trimethylazaniumyl)decyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C HLXQFVXURMXRPU-UHFFFAOYSA-L 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/10—Quaternary compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92679478A | 1978-07-21 | 1978-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD142547A5 true DD142547A5 (de) | 1980-07-02 |
Family
ID=25453730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79210690A DD142547A5 (de) | 1978-07-21 | 1979-01-29 | Verfahren zur herstellung von als neuromuskulaere blockierungsmittel verwendbaren verbindungen |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0010119A1 (it) |
| JP (1) | JPS5517367A (it) |
| AU (1) | AU522421B2 (it) |
| CA (1) | CA1125287A (it) |
| DD (1) | DD142547A5 (it) |
| DK (1) | DK34979A (it) |
| ES (1) | ES477257A1 (it) |
| FI (1) | FI790214A7 (it) |
| IE (1) | IE790108L (it) |
| IL (1) | IL56487A (it) |
| IT (1) | IT1202871B (it) |
| MC (1) | MC1240A1 (it) |
| PL (1) | PL121468B1 (it) |
| ZA (1) | ZA79253B (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8418303D0 (en) * | 1984-07-18 | 1984-08-22 | Wellcome Found | Compounds |
| BG41897A1 (en) * | 1985-07-19 | 1987-09-15 | Ivanov | Dichlormethylate of n, n'- 4, 10- dioxa- 3, 11- bis- tetrahydropapaverine and method for its preparation |
| US5240939A (en) * | 1991-10-31 | 1993-08-31 | Anaquest, Inc. | Nitrogen bridge tetrahydroisoquinolines |
| CN103880744A (zh) * | 2012-12-21 | 2014-06-25 | 常州工程职业技术学院 | 一种5’-甲氧基劳丹素的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2662083A (en) * | 1950-10-24 | 1953-12-08 | Allen & Hanburys Ltd | Heterocyclic polymethylene-bisquaternary ammonium salts and process for preparing same |
| GB863717A (en) * | 1958-07-03 | 1961-03-22 | Allen & Hanburys Ltd | Tetrahydropapaverine derivatives and their preparation |
| GB1125619A (en) * | 1965-11-15 | 1968-08-28 | Wellcome Found | Derivatives of bis-isoquinolines |
| AU506657B2 (en) * | 1975-12-10 | 1980-01-17 | Wellcome Foundation Limited, The | Isoquinoline derivatives |
| JPS5455577A (en) * | 1977-08-01 | 1979-05-02 | Masachiyuusetsutsu Gen Hosupit | Blocking agent of neuromuscle |
-
1979
- 1979-01-18 CA CA319,886A patent/CA1125287A/en not_active Expired
- 1979-01-22 ZA ZA79253A patent/ZA79253B/xx unknown
- 1979-01-23 IL IL56487A patent/IL56487A/xx unknown
- 1979-01-23 FI FI790214A patent/FI790214A7/fi unknown
- 1979-01-26 AU AU43688/79A patent/AU522421B2/en not_active Ceased
- 1979-01-26 DK DK34979A patent/DK34979A/da not_active Application Discontinuation
- 1979-01-26 MC MC791358A patent/MC1240A1/fr unknown
- 1979-01-29 IT IT19694/79A patent/IT1202871B/it active
- 1979-01-29 DD DD79210690A patent/DD142547A5/de unknown
- 1979-01-29 EP EP79100254A patent/EP0010119A1/en not_active Ceased
- 1979-01-29 ES ES477257A patent/ES477257A1/es not_active Expired
- 1979-01-30 JP JP960879A patent/JPS5517367A/ja active Pending
- 1979-01-30 PL PL1979213098A patent/PL121468B1/pl unknown
- 1979-01-30 IE IE790108A patent/IE790108L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL56487A0 (en) | 1979-03-12 |
| IL56487A (en) | 1983-05-15 |
| PL213098A1 (it) | 1980-03-24 |
| ZA79253B (en) | 1980-06-25 |
| IT7919694A0 (it) | 1979-01-29 |
| JPS5517367A (en) | 1980-02-06 |
| AU4368879A (en) | 1980-01-24 |
| MC1240A1 (fr) | 1979-10-26 |
| AU522421B2 (en) | 1982-06-03 |
| EP0010119A1 (en) | 1980-04-30 |
| CA1125287A (en) | 1982-06-08 |
| IT1202871B (it) | 1989-02-15 |
| DK34979A (da) | 1980-01-22 |
| IE790108L (en) | 1980-01-21 |
| ES477257A1 (es) | 1979-08-01 |
| FI790214A7 (fi) | 1980-01-22 |
| PL121468B1 (en) | 1982-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2655883C2 (it) | ||
| DE2658544C2 (de) | Carbostyrilderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1593579B1 (de) | Hydroxy-cyclohexylamine,deren physiologisch vertraeglichen Saeureadditionssalze und Verfahren zu ihrer Herstellung | |
| US4192877A (en) | Neuromuscular blocking agents | |
| DE2833505A1 (de) | Tetrahydro-isochinolin-derivate, verfahren zu deren herstellung und mittel enthaltend die derivate | |
| DE2635961A1 (de) | Therapeutisch wirksame verbindungen und verfahren zu ihrer herstellung | |
| DE2549889C2 (de) | 3,4-Dihydrocarbostyril-Derivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten | |
| US4235906A (en) | Bis-isoquinolinium compounds, compositions and methods of use | |
| DD142547A5 (de) | Verfahren zur herstellung von als neuromuskulaere blockierungsmittel verwendbaren verbindungen | |
| DE2449205C2 (de) | Substituierte Furylverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2101691A1 (de) | Isochinolinderivate | |
| DE2327193C3 (de) | N-(Diethylaminoethyl)-2-methoxy-5methylsulfonylbenzamid, seine Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2903917C2 (it) | ||
| DE1768671C3 (de) | N-(tert-Aminoalkyl)-2-alkylen-(oder -alkinyl)-oxybenzamide sowie ihre pharmazeutisch verträglichen Säureadditionssalze und quartären Ammoniumsalze | |
| DE2459630B2 (de) | 2-Pyrimidyl-aminomethylergolinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel | |
| DE2213044C3 (de) | Racemisches und optisch aktives 1 -(23-Dichlorphenoxy)-3-tert. - butylamino-2-propanol und ihre Salze, Verfahren zu deren Herstellung und Arzneimittel auf Basis dieser Verbindungen | |
| DE1232159B (de) | Verfahren zur Herstellung von trifluormethylgruppenhaltigen beta-Aminosaeureaniliden | |
| DE2130303C (de) | N Phosphorylbiguamde und diese enthaltende Arzneimittel | |
| DE2140550C3 (de) | 2-Benzoylalkylbenzomorphane, Verfahren zu ihrer Herstellung und Arzneimittel | |
| AT213395B (de) | Verfahren zur Herstellung des neuen β-Hydroxybuttersäure-cyclohexylamids | |
| SU1077569A3 (ru) | Способ получени производных изохинолини | |
| AT315870B (de) | Verfahren zur Herstellung von neuen Adenin-Derivaten und von deren Salzen | |
| AT339888B (de) | Verfahren zur herstellung von neuen basischen estern | |
| DE1595875C (de) | Phenothiazine und Verfahren zu deren Herstellung | |
| DE2130304C (de) | Phosphorylguamdine |