BE892860A - N-(1-phenylethyl)-n-(3,3-diphenylpropyl)-hydroxylamines et procede pour leur preparation - Google Patents

N-(1-phenylethyl)-n-(3,3-diphenylpropyl)-hydroxylamines et procede pour leur preparation Download PDF

Info

Publication number: BE892860A
Authority: BE; Belgium
Prior art keywords: emi; compound; diphenylpropyl; general formula; phenylethyl
Prior art date: 1981-04-22

Application number

BE0/207833A

Other languages

English (en)

French (fr)

Inventor

L Blaha

M Rajsner

V Trcka

J Muratova

M Vanecek

Original Assignee

Spofa Vereinigte Pharma Werke

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.)

1981-04-22

Filing date

1982-04-15

Publication date

1982-08-02

1982-04-15 Application filed by Spofa Vereinigte Pharma Werke filed Critical Spofa Vereinigte Pharma Werke

1982-08-02 Publication of BE892860A publication Critical patent/BE892860A/fr

Links

-1 1-PHENYLETHYL Chemical class 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 34
229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
239000011707 mineral Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 8
150000007522 mineralic acids Chemical class 0.000 claims description 8
150000007524 organic acids Chemical class 0.000 claims description 8
235000005985 organic acids Nutrition 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
239000003495 polar organic solvent Substances 0.000 claims description 6
238000006386 neutralization reaction Methods 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
IVUZQAPFQXQPLC-UHFFFAOYSA-N n-(3,3-diphenylpropyl)-n-(1-phenylethyl)hydroxylamine Chemical compound C=1C=CC=CC=1C(C)N(O)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 IVUZQAPFQXQPLC-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine Chemical class ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 claims 1
241000238876 Acari Species 0.000 claims 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000002585 base Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
238000001704 evaporation Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229960002602 fendiline Drugs 0.000 description 9
241000700159 Rattus Species 0.000 description 8
238000010828 elution Methods 0.000 description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
SLHSRCBFPHCSGL-UHFFFAOYSA-N (3-bromo-1-phenylpropyl)benzene Chemical compound C=1C=CC=CC=1C(CCBr)C1=CC=CC=C1 SLHSRCBFPHCSGL-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
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208000024891 symptom Diseases 0.000 description 5
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
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 4
WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
208000007101 Muscle Cramp Diseases 0.000 description 4
GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 4
102000002852 Vasopressins Human genes 0.000 description 4
108010004977 Vasopressins Proteins 0.000 description 4
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
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238000001035 drying Methods 0.000 description 4
229960001405 ergometrine Drugs 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
239000001530 fumaric acid Substances 0.000 description 4
208000019622 heart disease Diseases 0.000 description 4
239000007788 liquid Substances 0.000 description 4
210000004165 myocardium Anatomy 0.000 description 4
RRJRFNUPXQLYHX-UHFFFAOYSA-N n-(1-phenylethyl)hydroxylamine Chemical compound ONC(C)C1=CC=CC=C1 RRJRFNUPXQLYHX-UHFFFAOYSA-N 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
229960003726 vasopressin Drugs 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
IJXXDBXOFIZPAT-UHFFFAOYSA-N n-(3,3-diphenylpropyl)hydroxylamine Chemical compound C=1C=CC=CC=1C(CCNO)C1=CC=CC=C1 IJXXDBXOFIZPAT-UHFFFAOYSA-N 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
208000020446 Cardiac disease Diseases 0.000 description 2
241000282693 Cercopithecidae Species 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
241000699800 Cricetinae Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
210000000709 aorta Anatomy 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036770 blood supply Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000007865 diluting Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000036541 health Effects 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
230000000302 ischemic effect Effects 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000010453 quartz Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
PHGMUOJCQCLPBD-UHFFFAOYSA-N 1-(1-bromoethyl)-4-fluorobenzene Chemical compound CC(Br)C1=CC=C(F)C=C1 PHGMUOJCQCLPBD-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
206010005746 Blood pressure fluctuation Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
208000031229 Cardiomyopathies Diseases 0.000 description 1
208000001778 Coronary Occlusion Diseases 0.000 description 1
102000006835 Lamins Human genes 0.000 description 1
108010047294 Lamins Proteins 0.000 description 1
241000282553 Macaca Species 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
230000009471 action Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
230000002213 calciumantagonistic effect Effects 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
210000003748 coronary sinus Anatomy 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000151 deposition Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000003754 fetus Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
General Health & Medical Sciences (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BE0/207833A 1981-04-22 1982-04-15 N-(1-phenylethyl)-n-(3,3-diphenylpropyl)-hydroxylamines et procede pour leur preparation BE892860A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS813021A CS218402B1 (cs)	1981-04-22	1981-04-22	N- [ t-( 4-fluorfenyl) ethyl ] -N-(3,3-difenylpropyl) hydroxylamin a způsoby jeho přípravy

Publications (1)

Publication Number	Publication Date
BE892860A true BE892860A (fr)	1982-08-02

Family

ID=5369074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/207833A BE892860A (fr)	1981-04-22	1982-04-15	N-(1-phenylethyl)-n-(3,3-diphenylpropyl)-hydroxylamines et procede pour leur preparation

Country Status (3)

Country	Link
JP (1)	JPS57181042A (cs)
BE (1)	BE892860A (cs)
CS (1)	CS218402B1 (cs)

1981
- 1981-04-22 CS CS813021A patent/CS218402B1/cs unknown
1982
- 1982-04-15 BE BE0/207833A patent/BE892860A/fr not_active IP Right Cessation
- 1982-04-21 JP JP57065553A patent/JPS57181042A/ja active Pending

Also Published As

Publication number	Publication date
JPS57181042A (en)	1982-11-08
CS218402B1 (cs)	1983-02-25

Legal Events

Date

Code

Title

Description

1984-10-31

RE

Patent lapsed

Owner name: SPOFA SPOJENE PODNIKY PRO ZDRAVOTNICKOU VYROBU

Effective date: 19840415

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