NO773427L - Fremgangsmaate ved fremstilling av hydroxymethylpyridinestere - Google Patents

Fremgangsmaate ved fremstilling av hydroxymethylpyridinestere

Info

Publication number: NO773427L
Authority: NO; Norway
Prior art keywords: pyridine; acid; oxymethyl; carboxylic acid; general formula
Prior art date: 1976-10-08

Application number

NO773427A

Other languages

English (en)

Norwegian (no)

Inventor

Ferenc Noteisz

Mihaly Bartok

Karoly Felfoeldi

Egon Karpati

Laszlo Szporny

Original Assignee

Richter Gedeon Vegyeszet

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.)

1976-10-08

Filing date

1977-10-07

Publication date

1978-04-11

1977-10-07 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1978-04-11 Publication of NO773427L publication Critical patent/NO773427L/no

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title description 3
150000003839 salts Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 16
-1 9-xanthenyl group Chemical group 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
238000005917 acylation reaction Methods 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
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 2
239000003513 alkali Substances 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
230000010933 acylation Effects 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 9
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
ZKCCJRDNMQWHER-UHFFFAOYSA-N iodomethane;pyridin-3-ylmethyl 4-fluorobenzoate Chemical compound IC.C1=CC(F)=CC=C1C(=O)OCC1=CC=CN=C1 ZKCCJRDNMQWHER-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
YJSGCIHQZTUITL-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 2-chlorobenzoate Chemical compound IC.ClC1=CC=CC=C1C(=O)OCC1=CC=CC=N1 YJSGCIHQZTUITL-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229960001404 quinidine Drugs 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
206010061592 cardiac fibrillation Diseases 0.000 description 2
238000001816 cooling Methods 0.000 description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002600 fibrillogenic effect Effects 0.000 description 2
ZWJZPSWWYKMOEL-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 2-methoxybenzoate Chemical compound IC.COC1=CC=CC=C1C(=O)OCC1=CC=CC=N1 ZWJZPSWWYKMOEL-UHFFFAOYSA-N 0.000 description 2
DJFPRINBTRBLAL-UHFFFAOYSA-N iodomethane;pyridin-3-ylmethyl 3-(trifluoromethyl)benzoate Chemical compound IC.FC(F)(F)C1=CC=CC(C(=O)OCC=2C=NC=CC=2)=C1 DJFPRINBTRBLAL-UHFFFAOYSA-N 0.000 description 2
CEFHQJRVLJEHEQ-UHFFFAOYSA-N iodomethane;pyridin-3-ylmethyl 4-methoxybenzoate Chemical compound IC.C1=CC(OC)=CC=C1C(=O)OCC1=CC=CN=C1 CEFHQJRVLJEHEQ-UHFFFAOYSA-N 0.000 description 2
WLIDDEYMMUKIOH-UHFFFAOYSA-N iodomethane;pyridin-3-ylmethyl 9h-xanthene-9-carboxylate Chemical compound IC.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCC1=CC=CN=C1 WLIDDEYMMUKIOH-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
HKUGQAFOGIHIKX-UHFFFAOYSA-N pyridin-3-ylmethyl 4-fluorobenzoate;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(=O)OCC1=CC=CN=C1 HKUGQAFOGIHIKX-UHFFFAOYSA-N 0.000 description 2
KNRHJBMFDVYMPX-UHFFFAOYSA-N pyridin-4-ylmethyl 4-fluorobenzoate;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(=O)OCC1=CC=NC=C1 KNRHJBMFDVYMPX-UHFFFAOYSA-N 0.000 description 2
YJEVHCVINIDBSV-UHFFFAOYSA-N pyridin-4-ylmethyl 9h-xanthene-9-carboxylate;hydrochloride Chemical compound Cl.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCC1=CC=NC=C1 YJEVHCVINIDBSV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical class CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 description 1
CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 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
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000012190 activator Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000012304 carboxyl activating agent Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000006332 fluoro benzoyl group Chemical group 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
DRWGZELKLLEBJU-UHFFFAOYSA-N iodoethane;pyridin-3-ylmethyl 9h-xanthene-9-carboxylate Chemical compound CCI.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCC1=CC=CN=C1 DRWGZELKLLEBJU-UHFFFAOYSA-N 0.000 description 1
XDBSXNUHJGBBOJ-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 3-methoxybenzoate Chemical compound IC.COC1=CC=CC(C(=O)OCC=2N=CC=CC=2)=C1 XDBSXNUHJGBBOJ-UHFFFAOYSA-N 0.000 description 1
POHXYMBMHSDHHD-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 4-fluorobenzoate Chemical compound IC.C1=CC(F)=CC=C1C(=O)OCC1=CC=CC=N1 POHXYMBMHSDHHD-UHFFFAOYSA-N 0.000 description 1
RGVZIUGJHUJHAK-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 4-methoxybenzoate Chemical compound IC.C1=CC(OC)=CC=C1C(=O)OCC1=CC=CC=N1 RGVZIUGJHUJHAK-UHFFFAOYSA-N 0.000 description 1
HMUJPKVMYAJNCR-UHFFFAOYSA-N iodomethane;pyridin-2-ylmethyl 9h-xanthene-9-carboxylate Chemical compound IC.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCC1=CC=CC=N1 HMUJPKVMYAJNCR-UHFFFAOYSA-N 0.000 description 1
RKWBNYFTKOOOLB-UHFFFAOYSA-N iodomethane;pyridin-3-ylmethyl 3-methylbenzoate Chemical compound IC.CC1=CC=CC(C(=O)OCC=2C=NC=CC=2)=C1 RKWBNYFTKOOOLB-UHFFFAOYSA-N 0.000 description 1
WYIBJPLWHCRPEG-UHFFFAOYSA-N iodomethane;pyridin-4-ylmethyl 9h-xanthene-9-carboxylate Chemical compound IC.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCC1=CC=NC=C1 WYIBJPLWHCRPEG-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000005338 nitrobenzoic acids Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
KVUFDAYINYTZMN-UHFFFAOYSA-N pyridin-2-ylmethyl 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OCC1=CC=CC=N1 KVUFDAYINYTZMN-UHFFFAOYSA-N 0.000 description 1
BPNQTQDUQIZJOW-UHFFFAOYSA-N pyridin-3-ylmethanol;hydrochloride Chemical compound Cl.OCC1=CC=CN=C1 BPNQTQDUQIZJOW-UHFFFAOYSA-N 0.000 description 1
UUCYGVXKYAAOBS-UHFFFAOYSA-N pyridin-3-ylmethyl 2-methylbenzoate;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C(=O)OCC1=CC=CN=C1 UUCYGVXKYAAOBS-UHFFFAOYSA-N 0.000 description 1
KYXKVGPAZSUVDP-UHFFFAOYSA-N pyridin-3-ylmethyl 4-fluorobenzoate Chemical compound C1=CC(F)=CC=C1C(=O)OCC1=CC=CN=C1 KYXKVGPAZSUVDP-UHFFFAOYSA-N 0.000 description 1
VULJHCZCEOGYKG-UHFFFAOYSA-N pyridin-4-ylmethyl 2-methoxybenzoate;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C(=O)OCC1=CC=NC=C1 VULJHCZCEOGYKG-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO773427A 1976-10-08 1977-10-07 Fremgangsmaate ved fremstilling av hydroxymethylpyridinestere NO773427L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HURI000598 HU173917B (hu)	1976-10-08	1976-10-08	Sposob poluchenija novykh proizvodnykh benzoiloksimetil-piridina s antiaritmicheskim ehffektom i ikh additivnykhsolej s kislotami i ikh chetvertichnykh solej

Publications (1)

Publication Number	Publication Date
NO773427L true NO773427L (no)	1978-04-11

Family

ID=11001003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO773427A NO773427L (no)	1976-10-08	1977-10-07	Fremgangsmaate ved fremstilling av hydroxymethylpyridinestere

Country Status (21)

Country	Link
US (1)	US4184040A (fr)
JP (1)	JPS5346981A (fr)
AT (1)	AT357161B (fr)
AU (1)	AU508938B2 (fr)
BE (1)	BE859309A (fr)
CA (1)	CA1099271A (fr)
CH (1)	CH630612A5 (fr)
DE (1)	DE2745064A1 (fr)
FI (1)	FI772833A7 (fr)
FR (1)	FR2367074A1 (fr)
GB (1)	GB1583215A (fr)
HU (1)	HU173917B (fr)
IL (1)	IL52952A (fr)
IN (1)	IN146211B (fr)
NL (1)	NL7710792A (fr)
NO (1)	NO773427L (fr)
PT (1)	PT67105B (fr)
SE (1)	SE7710982L (fr)
SU (1)	SU686613A3 (fr)
YU (1)	YU239077A (fr)
ZA (1)	ZA775684B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57169166A (en) *	1981-04-09	1982-10-18	Yoshio Kawarazaki	Tatami core
US4348400A (en) *	1981-05-07	1982-09-07	Stauffer Chemical Company	Pyridylpropyl alkyl-substituted benzoates and their use as insect repellents
US4579850A (en) *	1985-02-25	1986-04-01	Stauffer Chemical Company	Halogenated esters of pyridine alkanols and their amine salts as insect repellents
US7352558B2 (en) *	2003-07-09	2008-04-01	Maxwell Technologies, Inc.	Dry particle based capacitor and methods of making same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2529865A (en) *	1947-04-05	1950-11-14	Searle & Co	Pyridylalkyl esters of aromatic substituted acetic acids
US3100775A (en) *	1959-04-01	1963-08-13	Searle & Co	alpha-phenyl(pyridyl or piperidyl)alkyl esters of (chloro or lower alkoxy)-benzoic acids and congeners
SE322214B (fr) *	1965-06-28	1970-04-06	Bofors Ab
FR2096629A1 (en) *	1969-12-24	1972-02-25	Develop Investissement	3-pyridylmethyl benzoates and phenylalkanoates - - with antirheumatic,analgesic,antiinflammatory antipyretic activity
DE2043455A1 (de) *	1970-09-02	1972-03-09	CH. Boehringer Sohn, 6507 Ingelheim	Neue l,2,3,6-tetrahydro-4-pyridylmethyl-carbonsäureester, sowie deren Säureadditionssalze und quarternären Ammoniumverbindungen

1976
- 1976-10-08 HU HURI000598 patent/HU173917B/hu unknown
1977
- 1977-09-19 IL IL52952A patent/IL52952A/xx unknown
- 1977-09-22 ZA ZA00775684A patent/ZA775684B/xx unknown
- 1977-09-23 GB GB39782/77A patent/GB1583215A/en not_active Expired
- 1977-09-26 FI FI772833A patent/FI772833A7/fi not_active Application Discontinuation
- 1977-09-26 CH CH1170077A patent/CH630612A5/de not_active IP Right Cessation
- 1977-09-29 AT AT693777A patent/AT357161B/de not_active IP Right Cessation
- 1977-09-30 SE SE7710982A patent/SE7710982L/xx not_active Application Discontinuation
- 1977-10-01 IN IN1467/CAL/77A patent/IN146211B/en unknown
- 1977-10-03 PT PT67105A patent/PT67105B/pt unknown
- 1977-10-03 BE BE181396A patent/BE859309A/fr unknown
- 1977-10-03 NL NL7710792A patent/NL7710792A/xx not_active Application Discontinuation
- 1977-10-05 US US05/839,605 patent/US4184040A/en not_active Expired - Lifetime
- 1977-10-05 YU YU02390/77A patent/YU239077A/xx unknown
- 1977-10-06 FR FR7730025A patent/FR2367074A1/fr active Granted
- 1977-10-06 DE DE19772745064 patent/DE2745064A1/de not_active Withdrawn
- 1977-10-07 JP JP12016077A patent/JPS5346981A/ja active Pending
- 1977-10-07 AU AU29462/77A patent/AU508938B2/en not_active Expired
- 1977-10-07 SU SU772529400A patent/SU686613A3/ru active
- 1977-10-07 NO NO773427A patent/NO773427L/no unknown
- 1977-10-07 CA CA288,370A patent/CA1099271A/fr not_active Expired

Also Published As

Publication number	Publication date
JPS5346981A (en)	1978-04-27
BE859309A (fr)	1978-02-01
DE2745064A1 (de)	1978-04-13
IL52952A0 (en)	1977-11-30
US4184040A (en)	1980-01-15
HU173917B (hu)	1979-09-28
PT67105A (en)	1977-11-01
YU239077A (en)	1982-08-31
AT357161B (de)	1980-06-25
SU686613A3 (ru)	1979-09-15
IN146211B (fr)	1979-03-24
NL7710792A (nl)	1978-04-11
CA1099271A (fr)	1981-04-14
SE7710982L (sv)	1978-04-09
FR2367074B1 (fr)	1983-01-07
AU508938B2 (en)	1980-04-17
AU2946277A (en)	1979-04-12
CH630612A5 (de)	1982-06-30
GB1583215A (en)	1981-01-21
FR2367074A1 (fr)	1978-05-05
ATA693777A (de)	1979-11-15
FI772833A7 (fi)	1978-04-09
PT67105B (en)	1979-03-13
ZA775684B (en)	1978-08-30
IL52952A (en)	1983-03-31

Publication	Publication Date	Title
US5118689A (en)	1992-06-02	Piperidine derivative and pharmaceutical composition containing the same
DK172337B1 (da)	1998-03-30	1-(Aryl- eller cyclohexyl)-alkylpiperidinforbindelser, farmaceutiske præparater med indhold af sådanne og anvendelse af forbindelserne til fremstilling af lægemidler
US4374990A (en)	1983-02-22	Cyclic diamine derivatives
EP0134124B1 (fr)	1987-10-28	Dérivés de la pipéridine
NO144262B (no)	1981-04-21	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme n-substituerte benzamidderivater
HU217433B (hu)	2000-01-28	Pirrolidinszármazékok, azokat tartalmazó gyógyszerkészítmények, és eljárás előállításukra
CA1322007C (fr)	1993-09-07	Composes piperidinyl disubstitues en 1,4, compositions pharmaceutiques de ceux-ci et methodes pour leur preparation
CA1295616C (fr)	1992-02-11	Agents antiarrhythmiques
US6355642B1 (en)	2002-03-12	Tetrahydrobenzindole compounds
NO140058B (no)	1979-03-19	Analogifremgangsmaate ved fremstilling av terapeutisk aktive substituerte piperidinoalkanol-oxim-derivater
JP2004506728A (ja)	2004-03-04	アミノアルコキシベンゾイル−ベンゾフランまたはベンゾチオフェン誘導体、その製造方法およびそれを含む組成物
US5916889A (en)	1999-06-29	1,4-disubstituted piperazines
US4684651A (en)	1987-08-04	Alkylenedioxybenzene and acid addition salts thereof useful as hypotensives
US4341893A (en)	1982-07-27	Quinazoline derivatives
JP3044055B2 (ja)	2000-05-22	１，２―エタンジオール誘導体およびその塩
EP0342635B1 (fr)	1994-08-17	Dérivés dés acids carboxyliques azacycliques leur préparation et application
JP3135170B2 (ja)	2001-02-13	アミノメチル置換２，３−ジヒドロピラノ〔２，３−ｂ〕ピリジン類
US5166211A (en)	1992-11-24	Method of using 1,4-disubstituted piperidinyl compounds in the treatment of coronary vasospasons and variant angina
US4442102A (en)	1984-04-10	1,5-Diphenylpyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing same
EP0441852B1 (fr)	1997-05-14	Antagonistes recepteurs muscariniques
US4184040A (en)	1980-01-15	Hydroxymethyl-pyridine esters and a process for the preparation thereof
NO151387B (no)	1984-12-17	Innstillingsinnretning for en elektronisk digitalindikator
US4256890A (en)	1981-03-17	3,4-Dihydrocarbostyril derivatives and process for producing the same
US4767767A (en)	1988-08-30	2-pyrrolidinylethyl-2-(7-trifluoromethyl-4-quinolyl-aminobenzoate having analgesic, antipyretic and anti-inflammatory activities
EP0052311A1 (fr)	1982-05-26	(Benzoylphényl-alkyl inférieur)-1 pipéridines et carbinols correspondants et leur préparation