CH634572A5 - Verfahren zur herstellung von pyridincarbonsaeureamiden. - Google Patents
Verfahren zur herstellung von pyridincarbonsaeureamiden. Download PDFInfo
- Publication number
- CH634572A5 CH634572A5 CH709078A CH709078A CH634572A5 CH 634572 A5 CH634572 A5 CH 634572A5 CH 709078 A CH709078 A CH 709078A CH 709078 A CH709078 A CH 709078A CH 634572 A5 CH634572 A5 CH 634572A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- salt
- mol
- acid
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 150000004885 piperazines Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BFDWWMRWLXGJNX-UHFFFAOYSA-N N-[(4-ethylphenyl)diazenyl]-N-methylacetamide Chemical compound CCC1=CC=C(N=NN(C)C(C)=O)C=C1 BFDWWMRWLXGJNX-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- SIEBMARYUSRWDM-UHFFFAOYSA-N piperazine;dihydrate Chemical compound O.O.C1CNCCN1 SIEBMARYUSRWDM-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- WCZVUZYEOJQHNJ-UHFFFAOYSA-M potassium;pyridine-3-carboxylate Chemical compound [K+].[O-]C(=O)C1=CC=CN=C1 WCZVUZYEOJQHNJ-UHFFFAOYSA-M 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 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
- 230000004580 weight loss Effects 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77EE2510A HU175075B (hu) | 1977-06-30 | 1977-06-30 | Sposob poluchenija piperazidov piridin-karbonovoj kisloty |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634572A5 true CH634572A5 (de) | 1983-02-15 |
Family
ID=10995734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH709078A CH634572A5 (de) | 1977-06-30 | 1978-06-29 | Verfahren zur herstellung von pyridincarbonsaeureamiden. |
Country Status (15)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985066A (en) * | 1975-05-15 | 1976-10-12 | S&S Corrugated Paper Machinery Co., Inc. | Single point means for slotter adjustment |
| DE10035908A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| US6953801B2 (en) | 2001-05-22 | 2005-10-11 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
| HRP20140621T1 (hr) * | 2009-08-24 | 2014-11-21 | Neuralstem, Inc. | Sinteza neurostimulativnog piperazina |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865828A (en) * | 1972-03-22 | 1975-02-11 | Egyt Gyogyszervegyeszeti Gyar | Pyridine derivatives having antidepressant activity |
| GB1451994A (en) * | 1973-07-20 | 1976-10-06 | Smithe Machine Co Inc F L | Method and apparatus for cutting and applying patches |
| JPS5144957A (ja) * | 1974-10-14 | 1976-04-16 | Matsushita Electric Works Ltd | Dejitarutokei |
| JPS5246080A (en) * | 1975-10-06 | 1977-04-12 | Taiho Yakuhin Kogyo Kk | Preparation of pyridinecarbonyl aminoalkyl thiols |
-
1977
- 1977-06-30 HU HU77EE2510A patent/HU175075B/hu not_active IP Right Cessation
-
1978
- 1978-06-20 CA CA305,894A patent/CA1103252A/en not_active Expired
- 1978-06-21 AT AT0453178A patent/AT365172B/de active
- 1978-06-26 SU SU782628948A patent/SU715023A3/ru active
- 1978-06-26 YU YU1499/78A patent/YU40711B/xx unknown
- 1978-06-26 DK DK285178A patent/DK148771C/da not_active IP Right Cessation
- 1978-06-26 FI FI782031A patent/FI66174C/fi not_active IP Right Cessation
- 1978-06-28 GB GB7828118A patent/GB2001062B/en not_active Expired
- 1978-06-28 DD DD78206341A patent/DD136136A5/xx not_active IP Right Cessation
- 1978-06-29 CH CH709078A patent/CH634572A5/de not_active IP Right Cessation
- 1978-06-29 PL PL1978208009A patent/PL110336B1/pl unknown
- 1978-06-29 CS CS784300A patent/CS199212B2/cs unknown
- 1978-06-29 JP JP7918978A patent/JPS5414985A/ja active Granted
- 1978-06-29 SE SE7807383A patent/SE429042B/sv not_active IP Right Cessation
- 1978-06-30 DE DE19782828888 patent/DE2828888A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5414985A (en) | 1979-02-03 |
| PL110336B1 (en) | 1980-07-31 |
| JPS6152826B2 (enrdf_load_stackoverflow) | 1986-11-14 |
| CS199212B2 (en) | 1980-07-31 |
| DE2828888A1 (de) | 1979-01-18 |
| DD136136A5 (de) | 1979-06-20 |
| PL208009A1 (pl) | 1979-05-07 |
| DK148771C (da) | 1986-03-10 |
| FI66174C (fi) | 1984-09-10 |
| DK285178A (da) | 1978-12-31 |
| SU715023A3 (ru) | 1980-02-05 |
| FI66174B (fi) | 1984-05-31 |
| SE7807383L (sv) | 1978-12-31 |
| GB2001062A (en) | 1979-01-24 |
| DK148771B (da) | 1985-09-23 |
| AT365172B (de) | 1981-12-28 |
| FI782031A7 (fi) | 1978-12-31 |
| YU40711B (en) | 1986-04-30 |
| SE429042B (sv) | 1983-08-08 |
| ATA453178A (de) | 1981-05-15 |
| HU175075B (hu) | 1980-05-28 |
| GB2001062B (en) | 1982-02-24 |
| YU149978A (en) | 1982-10-31 |
| CA1103252A (en) | 1981-06-16 |
| DE2828888C2 (enrdf_load_stackoverflow) | 1987-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |