SU686613A3 - Способ получени сложных эфиров оксиметилпиридина или их солей - Google Patents
Способ получени сложных эфиров оксиметилпиридина или их солейInfo
- Publication number
- SU686613A3 SU686613A3 SU772529400A SU2529400A SU686613A3 SU 686613 A3 SU686613 A3 SU 686613A3 SU 772529400 A SU772529400 A SU 772529400A SU 2529400 A SU2529400 A SU 2529400A SU 686613 A3 SU686613 A3 SU 686613A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- pyridine
- oxymethyl
- salts
- acid
- methyl iodide
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 17
- 238000000034 method Methods 0.000 title description 12
- 150000002148 esters Chemical class 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- -1 aliphatic ketones Chemical class 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 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 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000008020 evaporation Effects 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
- 238000002955 isolation Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 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 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- OGEMUNOAKYMNPW-UHFFFAOYSA-N FC1=CC=CC=C1.Cl Chemical compound FC1=CC=CC=C1.Cl OGEMUNOAKYMNPW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 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
- 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 1
- 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 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
- 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 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
- 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 1
- 238000002386 leaching Methods 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 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
- 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 1
- GSIQUKLFMDAHTF-UHFFFAOYSA-N pyridin-4-ylmethyl 3-methoxybenzoate;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)OCC=2C=CN=CC=2)=C1 GSIQUKLFMDAHTF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DOYPNUTUMHGKAT-UHFFFAOYSA-N pyridin-4-ylmethyl 4-methoxybenzoate;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(=O)OCC1=CC=NC=C1 DOYPNUTUMHGKAT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical class 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 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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 |
|---|---|
| SU686613A3 true SU686613A3 (ru) | 1979-09-15 |
Family
ID=11001003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772529400A SU686613A3 (ru) | 1976-10-08 | 1977-10-07 | Способ получени сложных эфиров оксиметилпиридина или их солей |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4184040A (enExample) |
| JP (1) | JPS5346981A (enExample) |
| AT (1) | AT357161B (enExample) |
| AU (1) | AU508938B2 (enExample) |
| BE (1) | BE859309A (enExample) |
| CA (1) | CA1099271A (enExample) |
| CH (1) | CH630612A5 (enExample) |
| DE (1) | DE2745064A1 (enExample) |
| FI (1) | FI772833A7 (enExample) |
| FR (1) | FR2367074A1 (enExample) |
| GB (1) | GB1583215A (enExample) |
| HU (1) | HU173917B (enExample) |
| IL (1) | IL52952A (enExample) |
| IN (1) | IN146211B (enExample) |
| NL (1) | NL7710792A (enExample) |
| NO (1) | NO773427L (enExample) |
| PT (1) | PT67105B (enExample) |
| SE (1) | SE7710982L (enExample) |
| SU (1) | SU686613A3 (enExample) |
| YU (1) | YU239077A (enExample) |
| ZA (1) | ZA775684B (enExample) |
Families Citing this family (4)
| 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)
| 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 (enExample) * | 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/xx unknown
- 1977-10-03 NL NL7710792A patent/NL7710792A/xx not_active Application Discontinuation
- 1977-10-05 YU YU02390/77A patent/YU239077A/xx unknown
- 1977-10-05 US US05/839,605 patent/US4184040A/en not_active Expired - Lifetime
- 1977-10-06 FR FR7730025A patent/FR2367074A1/fr active Granted
- 1977-10-06 DE DE19772745064 patent/DE2745064A1/de not_active Withdrawn
- 1977-10-07 AU AU29462/77A patent/AU508938B2/en not_active Expired
- 1977-10-07 JP JP12016077A patent/JPS5346981A/ja active Pending
- 1977-10-07 CA CA288,370A patent/CA1099271A/en not_active Expired
- 1977-10-07 SU SU772529400A patent/SU686613A3/ru active
- 1977-10-07 NO NO773427A patent/NO773427L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4184040A (en) | 1980-01-15 |
| ZA775684B (en) | 1978-08-30 |
| FI772833A7 (fi) | 1978-04-09 |
| JPS5346981A (en) | 1978-04-27 |
| IN146211B (enExample) | 1979-03-24 |
| NO773427L (no) | 1978-04-11 |
| GB1583215A (en) | 1981-01-21 |
| AU2946277A (en) | 1979-04-12 |
| CA1099271A (en) | 1981-04-14 |
| ATA693777A (de) | 1979-11-15 |
| YU239077A (en) | 1982-08-31 |
| IL52952A (en) | 1983-03-31 |
| PT67105A (en) | 1977-11-01 |
| FR2367074B1 (enExample) | 1983-01-07 |
| SE7710982L (sv) | 1978-04-09 |
| NL7710792A (nl) | 1978-04-11 |
| IL52952A0 (en) | 1977-11-30 |
| HU173917B (hu) | 1979-09-28 |
| DE2745064A1 (de) | 1978-04-13 |
| BE859309A (fr) | 1978-02-01 |
| CH630612A5 (de) | 1982-06-30 |
| FR2367074A1 (fr) | 1978-05-05 |
| PT67105B (en) | 1979-03-13 |
| AT357161B (de) | 1980-06-25 |
| AU508938B2 (en) | 1980-04-17 |
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