FI78682C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar. - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar. Download PDFInfo
- Publication number
- FI78682C FI78682C FI840500A FI840500A FI78682C FI 78682 C FI78682 C FI 78682C FI 840500 A FI840500 A FI 840500A FI 840500 A FI840500 A FI 840500A FI 78682 C FI78682 C FI 78682C
- Authority
- FI
- Finland
- Prior art keywords
- general formula
- compound
- configuration
- acid addition
- halogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- -1 oxime ethers Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- 230000003288 anthiarrhythmic effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000000202 analgesic effect Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003257 anti-anginal effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 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 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229960004194 lidocaine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 3
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940039750 aconitine Drugs 0.000 description 3
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
- VJQULJPYVAJZKN-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.CC(C)N(C(C)C)CCCCl VJQULJPYVAJZKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PAPDDSQMDJLMMR-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-n-[3-(4-methylpiperazin-1-yl)propoxy]cyclohexan-1-imine Chemical compound C1CN(C)CCN1CCCON=C1C(CC=2C=CC(Cl)=CC=2)CCCC1 PAPDDSQMDJLMMR-UHFFFAOYSA-N 0.000 description 1
- ABDIQFMIEMQAQS-UHFFFAOYSA-N 3-[(2-benzylcyclohexylidene)amino]oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCC1CC1=CC=CC=C1 ABDIQFMIEMQAQS-UHFFFAOYSA-N 0.000 description 1
- RFZXCSKMSPTCIS-UHFFFAOYSA-N 3-[[2-[(2-methoxyphenyl)methylidene]cyclohexylidene]amino]oxy-n,n,2-trimethylpropan-1-amine Chemical compound COC1=CC=CC=C1C=C1C(=NOCC(C)CN(C)C)CCCC1 RFZXCSKMSPTCIS-UHFFFAOYSA-N 0.000 description 1
- QTBORURRHPKIKH-UHFFFAOYSA-N 3-[[2-[(4-chlorophenyl)methyl]cyclohexylidene]amino]oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCC1CC1=CC=C(Cl)C=C1 QTBORURRHPKIKH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU41483 | 1983-02-08 | ||
| HU83414A HU188250B (en) | 1983-02-08 | 1983-02-08 | Process for producing of basical oxim-ethers |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI840500A0 FI840500A0 (fi) | 1984-02-07 |
| FI840500A7 FI840500A7 (fi) | 1984-08-09 |
| FI78682B FI78682B (fi) | 1989-05-31 |
| FI78682C true FI78682C (fi) | 1989-09-11 |
Family
ID=10949510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI840500A FI78682C (fi) | 1983-02-08 | 1984-02-07 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4727074A (en, 2012) |
| JP (1) | JPS59172454A (en, 2012) |
| AT (1) | AT389872B (en, 2012) |
| AU (1) | AU562028B2 (en, 2012) |
| BE (1) | BE898835A (en, 2012) |
| CA (1) | CA1247103A (en, 2012) |
| CH (1) | CH660004A5 (en, 2012) |
| DE (1) | DE3404481A1 (en, 2012) |
| DK (1) | DK160299C (en, 2012) |
| ES (2) | ES8606258A1 (en, 2012) |
| FI (1) | FI78682C (en, 2012) |
| FR (1) | FR2540493B1 (en, 2012) |
| GB (1) | GB2134904B (en, 2012) |
| GR (1) | GR81458B (en, 2012) |
| HU (1) | HU188250B (en, 2012) |
| IL (1) | IL70885A (en, 2012) |
| NL (1) | NL8400376A (en, 2012) |
| PH (1) | PH20863A (en, 2012) |
| PL (1) | PL141942B1 (en, 2012) |
| SE (1) | SE465675B (en, 2012) |
| SU (1) | SU1353774A1 (en, 2012) |
| YU (1) | YU21984A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU197205B (en) * | 1984-07-10 | 1989-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of medical compositions against angine |
| DE3620166A1 (de) * | 1986-06-14 | 1987-12-17 | Bayer Ag | Verfahren zur herstellung von hydroxybenzaldoxim-o-ethern |
| HU202195B (en) * | 1987-12-31 | 1991-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new substituted styrene derivatives and medical compositions comprising such compounds |
| HUT67314A (en) * | 1993-04-09 | 1995-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for prepg. new trisubstituted cykloalkane deriv.s and pharmaceutical compn.s contg. them |
| UA65635C2 (uk) * | 1998-09-03 | 2004-04-15 | Н-Гене Кутато Кфт. | НЕНАСИЧЕНІ ПОХІДНІ ГІДРОКСИМОВОЇ КИСЛОТИ, ЩО МАЮТЬ ВЛАСТИВОСТІ ІНГІБІТОРІВ NAD<sup>+</sup>-ADP-РИБОЗИЛТРАНСФЕРАЗИ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU169298B (en, 2012) * | 1974-09-24 | 1976-11-28 | ||
| GB1493222A (en) * | 1976-01-27 | 1977-11-30 | Egyt Gyogyszervegyeszeti Gyar | Cycloalkanone oxime ethers and process for the preparation thereof |
| US4083978A (en) * | 1976-01-27 | 1978-04-11 | Egyt Gyogyszervegyeszeti Gyar | Oxime ethers |
| HU180739B (en) * | 1979-07-03 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing basic oxime-ethers |
-
1983
- 1983-02-08 HU HU83414A patent/HU188250B/hu not_active IP Right Cessation
-
1984
- 1984-02-03 PH PH30201A patent/PH20863A/en unknown
- 1984-02-03 BE BE1/010952A patent/BE898835A/fr not_active IP Right Cessation
- 1984-02-06 AT AT0036984A patent/AT389872B/de not_active IP Right Cessation
- 1984-02-06 CH CH546/84A patent/CH660004A5/de not_active IP Right Cessation
- 1984-02-07 SE SE8400629A patent/SE465675B/sv not_active IP Right Cessation
- 1984-02-07 NL NL8400376A patent/NL8400376A/nl not_active Application Discontinuation
- 1984-02-07 IL IL70885A patent/IL70885A/xx unknown
- 1984-02-07 FR FR8401833A patent/FR2540493B1/fr not_active Expired
- 1984-02-07 GB GB08403233A patent/GB2134904B/en not_active Expired
- 1984-02-07 FI FI840500A patent/FI78682C/fi not_active IP Right Cessation
- 1984-02-07 AU AU24248/84A patent/AU562028B2/en not_active Ceased
- 1984-02-07 YU YU00219/84A patent/YU21984A/xx unknown
- 1984-02-07 DK DK054684A patent/DK160299C/da not_active IP Right Cessation
- 1984-02-07 PL PL1984246099A patent/PL141942B1/pl unknown
- 1984-02-07 CA CA000446931A patent/CA1247103A/en not_active Expired
- 1984-02-08 DE DE19843404481 patent/DE3404481A1/de not_active Withdrawn
- 1984-02-08 JP JP59021513A patent/JPS59172454A/ja active Pending
- 1984-02-08 ES ES529565A patent/ES8606258A1/es not_active Expired
- 1984-02-08 GR GR73746A patent/GR81458B/el unknown
- 1984-02-08 US US06/578,286 patent/US4727074A/en not_active Expired - Fee Related
- 1984-02-08 SU SU843702235A patent/SU1353774A1/ru active
-
1985
- 1985-06-17 ES ES544287A patent/ES8604122A1/es not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2637737B2 (ja) | 新規な薬剤 | |
| CH621329A5 (en, 2012) | ||
| AT394552B (de) | Verfahren zur herstellung des neuen n-(2-(4-fluor-phenyl)-1-methyl)-aethyl-n-methyl- propinylamin und isomeren und salzen desselben | |
| CA1116611A (en) | Imidazole derivatives exhibiting anticonvulsant activity | |
| DE2835701C2 (de) | Cycloalkylidenmethylphenylessigsäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen | |
| US4327022A (en) | Heterocyclic alkyl naphthols | |
| US4202892A (en) | Biocidal methyladamantyl hydrazines and pharmaceutical compositions containing them | |
| NZ232258A (en) | 1-benzyl-indazol-3-yl methoxy acetic acid derivatives; preparatory processes pharmaceutical compositions and intermediates | |
| FI78682C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar. | |
| US4169108A (en) | 5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols | |
| HU191094B (en) | Process for producing insoquinoline derivatives and pharmaceutical compositions containing them | |
| IE911744A1 (en) | N-substituted trifluoromethylphenyltetrahydropyridines, process for the preparation thereof, intermediates in said process and pharmaceutical compositions containing them | |
| EP0346791A1 (en) | 1,2-diarylethylamines for treatment of neurotoxic injury | |
| US3530126A (en) | N-heterocyclic substituted cyclohexanes | |
| NL8003846A (nl) | Nieuwe oxime-ethers, hun bereiding en farmaceutische samenstellingen, die ze bevatten. | |
| US3526671A (en) | Aminoalkylated oximes of dibenzo(a,d)cyclohepten-5-ones | |
| DE3706585A1 (de) | Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung | |
| US4206217A (en) | 3-[4-(1,3-Diazacycloalken-2-yl)-phenyl]-1,2-benzisothiazoles, their manufacture, and drugs containing these compounds | |
| US4129658A (en) | 4-Styryl-hexahydro-4-indolinols | |
| US4139621A (en) | N-(4-substituted-3,5-dichloro-phenyl)-piperazines | |
| PL112249B1 (en) | Process for preparing novel derivatives of 1-/3-/3,4,5-trimethoxyphenoxy/-2-hydroxypropyl/-4-arylpiperazine | |
| CH644364A5 (de) | 4-(naphthalinyloxy)piperidin-derivate. | |
| EP0152556A1 (de) | Aminopropanolderivate von substituierten 2-Hydroxy-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel | |
| US3037982A (en) | Phenylpiperazinylalkyl propionanilides | |
| US3701786A (en) | Dibenzofuranyl-aminoalcohols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: EGIS GYOGYSZERGYAR |