CH427777A - Verfahren zur Herstellung von Phenoxyalkylaminoguanidinen - Google Patents

Verfahren zur Herstellung von Phenoxyalkylaminoguanidinen

Info

Publication number: CH427777A
Authority: CH; Switzerland
Prior art keywords: parts; weight; guanidine; ethylamino; sulfate
Prior art date: 1962-03-15

Application number

CH330763A

Other languages

German (de)

English (en)

Inventor

Augstein Joachim

Charles Austin William

Joseph Boscott Ronald

Hubert Hunter William

Mary Green Sheila

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1962-03-15

Filing date

1963-03-15

Publication date

1967-01-15

1962-03-15 Priority claimed from GB999862A external-priority patent/GB1011286A/en

1963-03-15 Application filed by Pfizer filed Critical Pfizer

1967-01-15 Publication of CH427777A publication Critical patent/CH427777A/de

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 44
239000002904 solvent Substances 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 12
239000012458 free base Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims 1
-1 phenoxyalkyl halide Chemical class 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 12
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 11
NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
229960004198 guanidine Drugs 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
CJHKWIFDLHQWCU-UHFFFAOYSA-N 1-(2-chloroethoxy)-2-methoxybenzene Chemical compound COC1=CC=CC=C1OCCCl CJHKWIFDLHQWCU-UHFFFAOYSA-N 0.000 description 4
SJCNWNXOLZOSTD-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)ethylamino]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.CC1=C(OCCNNC(=N)N)C(=CC=C1)C SJCNWNXOLZOSTD-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
MNSGECSGBCXBAD-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)ethylhydrazine Chemical compound CC1=CC=CC(C)=C1OCCNN MNSGECSGBCXBAD-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
HSCZQRYUSCLPKK-UHFFFAOYSA-N 3-phenoxypropylhydrazine Chemical compound NNCCCOC1=CC=CC=C1 HSCZQRYUSCLPKK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229960002624 bretylium tosilate Drugs 0.000 description 2
KVWNWTZZBKCOPM-UHFFFAOYSA-M bretylium tosylate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC[N+](C)(C)CC1=CC=CC=C1Br KVWNWTZZBKCOPM-UHFFFAOYSA-M 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 2
229960003602 guanethidine Drugs 0.000 description 2
XIHXRRMCNSMUET-UHFFFAOYSA-N guanoclor Chemical compound NC(=N)NNCCOC1=C(Cl)C=CC=C1Cl XIHXRRMCNSMUET-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
JJXWKXZOHOUFCX-UHFFFAOYSA-N methylhydrazine;hydrate Chemical compound O.CNN JJXWKXZOHOUFCX-UHFFFAOYSA-N 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000002040 relaxant effect Effects 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
KUQFCVUCTWAPEO-UHFFFAOYSA-N 1,2-dimethylhydrazine hydrate Chemical compound O.CNNC KUQFCVUCTWAPEO-UHFFFAOYSA-N 0.000 description 1
VULUPRKDRIRLLH-UHFFFAOYSA-N 1-(2-chloroethoxy)-2-methylbenzene Chemical compound CC1=CC=CC=C1OCCCl VULUPRKDRIRLLH-UHFFFAOYSA-N 0.000 description 1
BYJBIUUBBIMSQO-UHFFFAOYSA-N 1-chloro-2-(2-chloroethoxy)benzene Chemical compound ClCCOC1=CC=CC=C1Cl BYJBIUUBBIMSQO-UHFFFAOYSA-N 0.000 description 1
HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
PNBGLYIFRCIUHW-UHFFFAOYSA-N 2-(2,5-dichlorophenoxy)ethylhydrazine Chemical compound NNCCOC1=CC(Cl)=CC=C1Cl PNBGLYIFRCIUHW-UHFFFAOYSA-N 0.000 description 1
ISFRQPYFMIVDTO-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)ethylhydrazine Chemical compound NNCCOC1=C(Cl)C=CC=C1Cl ISFRQPYFMIVDTO-UHFFFAOYSA-N 0.000 description 1
RQGVZXGJKYJQSN-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1OCCBr RQGVZXGJKYJQSN-UHFFFAOYSA-N 0.000 description 1
MSKAVXYLXIUCJP-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1OCCBr MSKAVXYLXIUCJP-UHFFFAOYSA-N 0.000 description 1
JFOWYGCPBNNSHQ-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(OCCBr)=C1 JFOWYGCPBNNSHQ-UHFFFAOYSA-N 0.000 description 1
QJLAEVDWQPIZHI-UHFFFAOYSA-N 2-(2-chloroethoxy)-1,3-dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OCCCl QJLAEVDWQPIZHI-UHFFFAOYSA-N 0.000 description 1
UVDWJORAOPBIIV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethylhydrazine Chemical compound COC1=CC=CC=C1OCCNN UVDWJORAOPBIIV-UHFFFAOYSA-N 0.000 description 1
FSKAOASCCDEIJN-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)ethylhydrazine Chemical compound NNCCOC1=CC=C(Cl)C(Cl)=C1 FSKAOASCCDEIJN-UHFFFAOYSA-N 0.000 description 1
RZJKERFDQZMLSH-UHFFFAOYSA-N 2-(4-chlorobutoxy)phenol Chemical compound ClCCCCOC1=C(C=CC=C1)O RZJKERFDQZMLSH-UHFFFAOYSA-N 0.000 description 1
VXBPGXLKMKKQJX-UHFFFAOYSA-N 2-[2-(2,6-dichlorophenoxy)ethylamino]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(=N)NNCCOC1=C(Cl)C=CC=C1Cl VXBPGXLKMKKQJX-UHFFFAOYSA-N 0.000 description 1
JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
JVQBFZMPFQQOMQ-UHFFFAOYSA-N 2-phenoxyethylhydrazine Chemical compound NNCCOC1=CC=CC=C1 JVQBFZMPFQQOMQ-UHFFFAOYSA-N 0.000 description 1
NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
SQMJIYQANBYVEL-UHFFFAOYSA-N 4-(2-bromoethoxy)-1,2-dichlorobenzene Chemical compound ClC1=CC=C(OCCBr)C=C1Cl SQMJIYQANBYVEL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
SLJHGZKIOMJADE-UHFFFAOYSA-N C(CCC)C1=C(OCCCl)C=CC=C1 Chemical compound C(CCC)C1=C(OCCCl)C=CC=C1 SLJHGZKIOMJADE-UHFFFAOYSA-N 0.000 description 1
206010010144 Completed suicide Diseases 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
206010067598 Neurogenic hypertension Diseases 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003043 adrenergic neuron blocking agent Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
108091008698 baroreceptors Proteins 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000002146 bilateral effect Effects 0.000 description 1
FCCCRBDJBTVFSJ-UHFFFAOYSA-N butanehydrazide Chemical compound CCCC(=O)NN FCCCRBDJBTVFSJ-UHFFFAOYSA-N 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 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
239000000155 melt Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
210000001774 pressoreceptor Anatomy 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 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

- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH330763A 1962-03-15 1963-03-15 Verfahren zur Herstellung von Phenoxyalkylaminoguanidinen CH427777A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB999862A GB1011286A (en)	1962-03-15	1962-03-15	Amino guanidines
GB2807562		1962-07-20

Publications (1)

Publication Number	Publication Date
CH427777A true CH427777A (de)	1967-01-15

Family

ID=26243320

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH330763A CH427777A (de)	1962-03-15	1963-03-15	Verfahren zur Herstellung von Phenoxyalkylaminoguanidinen

Country Status (6)

Country	Link
CH (1)	CH427777A (fr)
DE (1)	DE1468479A1 (fr)
DK (1)	DK107418C (fr)
ES (1)	ES286123A1 (fr)
FR (1)	FR3337M (fr)
SE (1)	SE310359B (fr)

1963
- 1963-03-14 DE DE19631468479 patent/DE1468479A1/de active Pending
- 1963-03-14 DK DK117163AA patent/DK107418C/da active
- 1963-03-15 CH CH330763A patent/CH427777A/de unknown
- 1963-03-15 ES ES286123A patent/ES286123A1/es not_active Expired
- 1963-03-15 FR FR928173A patent/FR3337M/fr not_active Expired
- 1963-03-15 SE SE2836/63A patent/SE310359B/xx unknown

Also Published As

Publication number	Publication date
DK107418C (da)	1967-05-29
SE310359B (fr)	1969-04-28
DE1468479A1 (de)	1968-11-28
ES286123A1 (es)	1963-07-01
FR3337M (fr)	1965-05-31

Publication	Publication Date	Title
DD202152A5 (de)	1983-08-31	Verfahren zur herstellung von phenylpiperazinderivaten
DD148050A5 (de)	1981-05-06	Verfahren zur herstellung neuer n-aryl-bzw.benzimidazolione
DE1668420A1 (de)	1970-06-25	N-substituierte Perfluoralkylsulfonamide
DE1720019A1 (de)	1972-03-30	Pyrrylaminoketonderivate und Verfahren zu ihrer Herstellung
DE3102769A1 (de)	1982-02-04	"bis-moranolinderivate"
DE2155132A1 (de)	1972-06-29	l-(2-Hydroxy-3-phenoxy- oder-phenylthic~propyl)-piperazin-Derivate
DE2060614C3 (de)	1980-06-19	9a-Methyl-23,9,9a-tetrahydro- oxazolo- [3,2,-a] indole
DD140041B1 (de)	1986-05-07	Verfahren zur herstellung von langkettigen n-alkyldimethylmorpholinen
CH427777A (de)	1967-01-15	Verfahren zur Herstellung von Phenoxyalkylaminoguanidinen
DE2166270C3 (de)	1975-10-09	Nicotinoylaminoäthansulfonyl-2amino-thiazol
DE2942832C2 (de)	1984-11-22	Carbamoylpiperazinderivate
DE2144077C3 (de)	1974-02-14	Neue Hydroxyäthylaminoalkylpiperazine und Verfahren zu deren Herstellung
DE2512702C2 (de)	1982-09-23	Substituierte 1-Amino-3-phenyl-indole, deren Salze und Verfahren zu ihrer Herstellung
CH474490A (de)	1969-06-30	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
AT298457B (de)	1972-05-10	Verfahren zur Herstellung von neuen 1-(4'-Acylaminophenoxy)-2-hydroxy-3-aminopropanen und von deren Säureadditionssalzen
DE1220434B (de)	1966-07-07	Verfahren zur Herstellung von am kernstaendigen Stickstoffatom substituierten 2-Sulfamyl-4-trifluormethylanilin-Verbindungen
AT257058B (de)	1967-09-25	Verfahren zur Herstellung des neuen bis-Pyridylmethyl-disulfids
AT334341B (de)	1976-01-10	Verfahren zur herstellung von neuen alpha- (1-bis-arylalkylaminoalkyl) -aralkoxybenzylalkoholen
DE1493994A1 (de)	1969-10-02	Verfahren zur Herstellung von Phenoxyessigsaeureverbindungen
DE1620206C (de)	1972-10-12	N-Cyclopropylmethyl-6,14-endo-äthanotetrahydronororipavine und ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
AT247353B (de)	1966-06-10	Verfahren zur Herstellung neuer 2-Chlor-4-azaphenthiazinderivate
DE2515548A1 (de)	1975-10-23	Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellung
AT338768B (de)	1977-09-12	Verfahren zur herstellung von neuen phenoxyalkansaureamiden
AT359479B (de)	1980-11-10	Verfahren zur herstellung von neuen benzoe- saeuren und deren estern und salzen
AT228798B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen