JPH0859619A - ２−ハロゲノピリジンアルデヒド類の製造方法および新規な２−ハロゲノピリジンアルデヒド類 - Google Patents
２−ハロゲノピリジンアルデヒド類の製造方法および新規な２−ハロゲノピリジンアルデヒド類Info
- Publication number
- JPH0859619A JPH0859619A JP7229616A JP22961695A JPH0859619A JP H0859619 A JPH0859619 A JP H0859619A JP 7229616 A JP7229616 A JP 7229616A JP 22961695 A JP22961695 A JP 22961695A JP H0859619 A JPH0859619 A JP H0859619A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- alkoxy
- cyano
- halogen
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- -1 C 1 -C 8 - alkyl Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- QSLGTPPMJGXGBU-UHFFFAOYSA-N 2-chloropyridine-3,5-dicarbaldehyde Chemical compound ClC1=NC=C(C=O)C=C1C=O QSLGTPPMJGXGBU-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- ROSCFXKNBQZLFC-UHFFFAOYSA-N 5,6-dichloropyridine-3-carbaldehyde Chemical compound ClC1=CC(C=O)=CN=C1Cl ROSCFXKNBQZLFC-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000000126 substance Substances 0.000 description 40
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000012043 crude product Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- JMLGDNLEUWDYJI-UHFFFAOYSA-N 2-chloro-5-formylpyridine-3-carbonitrile Chemical compound ClC1=NC=C(C=O)C=C1C#N JMLGDNLEUWDYJI-UHFFFAOYSA-N 0.000 description 3
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJHUAOWEHGGIRB-UHFFFAOYSA-N 2,5-dichloropyridine-3-carbaldehyde Chemical compound ClC1=CN=C(Cl)C(C=O)=C1 IJHUAOWEHGGIRB-UHFFFAOYSA-N 0.000 description 2
- PGWZEMYEIXWVBM-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine-3-carbaldehyde Chemical compound ClCC1=CN=C(Cl)C(C=O)=C1 PGWZEMYEIXWVBM-UHFFFAOYSA-N 0.000 description 2
- IZDJJYRXECMSLX-UHFFFAOYSA-N 2-chloro-5-methylpyridine-3-carbaldehyde Chemical compound CC1=CN=C(Cl)C(C=O)=C1 IZDJJYRXECMSLX-UHFFFAOYSA-N 0.000 description 2
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 2
- VPGXPWHNPQONBA-UHFFFAOYSA-N 2-ethylidenepropanedinitrile Chemical compound CC=C(C#N)C#N VPGXPWHNPQONBA-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- WKFMHXZXCCJSJK-UHFFFAOYSA-N 2-hydroxybut-3-enenitrile Chemical compound C=CC(O)C#N WKFMHXZXCCJSJK-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PJOUURZOYJMYPA-UHFFFAOYSA-N OClC#N Chemical compound OClC#N PJOUURZOYJMYPA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- KFISEQOLPGMMBB-UHFFFAOYSA-N pyridine-3,5-dicarbaldehyde Chemical compound O=CC1=CN=CC(C=O)=C1 KFISEQOLPGMMBB-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IHXNSHZBFXGOJM-HWKANZROSA-N (e)-2-methylbut-2-enenitrile Chemical compound C\C=C(/C)C#N IHXNSHZBFXGOJM-HWKANZROSA-N 0.000 description 1
- TZRCAFZIOSMMHX-VQHVLOKHSA-N (e)-3-phenylbut-2-enenitrile Chemical compound N#C\C=C(/C)C1=CC=CC=C1 TZRCAFZIOSMMHX-VQHVLOKHSA-N 0.000 description 1
- CQWHLNCODHOFCT-XBXARRHUSA-N (e)-4-phenylbut-3-enenitrile Chemical compound N#CC\C=C\C1=CC=CC=C1 CQWHLNCODHOFCT-XBXARRHUSA-N 0.000 description 1
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- MEHLEOUIWVWVBF-UHFFFAOYSA-N 1-cyanoprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)C#N MEHLEOUIWVWVBF-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- HWUQKELWCYCAFU-UHFFFAOYSA-N 2,4-dichloro-5-formylpyridine-3-carbonitrile Chemical compound ClC1=NC=C(C=O)C(Cl)=C1C#N HWUQKELWCYCAFU-UHFFFAOYSA-N 0.000 description 1
- TYPVHTOETJVYIV-UHFFFAOYSA-N 2,4-dichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1 TYPVHTOETJVYIV-UHFFFAOYSA-N 0.000 description 1
- QAZULYBTLQWYAH-UHFFFAOYSA-N 2,4-dichloropyridine-3,5-dicarbaldehyde Chemical compound ClC1=NC=C(C=O)C(Cl)=C1C=O QAZULYBTLQWYAH-UHFFFAOYSA-N 0.000 description 1
- GWBHJHIZHNTJLA-UHFFFAOYSA-N 2,4-dichloropyridine-3-carbaldehyde Chemical compound ClC1=CC=NC(Cl)=C1C=O GWBHJHIZHNTJLA-UHFFFAOYSA-N 0.000 description 1
- LBTQCPWBQJYQLI-UHFFFAOYSA-N 2-(1-methoxyethylidene)propanedinitrile Chemical compound COC(C)=C(C#N)C#N LBTQCPWBQJYQLI-UHFFFAOYSA-N 0.000 description 1
- ZVOMMPYHGITOEF-UHFFFAOYSA-N 2-(1-phenylethylidene)propanedinitrile Chemical compound N#CC(C#N)=C(C)C1=CC=CC=C1 ZVOMMPYHGITOEF-UHFFFAOYSA-N 0.000 description 1
- XYHGGVNAIYUAJW-UHFFFAOYSA-N 2-chloro-1h-pyridine-2,3-dicarbaldehyde Chemical compound O=CC1(Cl)NC=CC=C1C=O XYHGGVNAIYUAJW-UHFFFAOYSA-N 0.000 description 1
- RKLRUFWPFMHXHD-UHFFFAOYSA-N 2-chloro-1h-pyridine-2-carbaldehyde Chemical compound O=CC1(Cl)NC=CC=C1 RKLRUFWPFMHXHD-UHFFFAOYSA-N 0.000 description 1
- PLVSCDNPHXSGGB-UHFFFAOYSA-N 2-chloro-4-phenylpyridine-3,5-dicarbaldehyde Chemical compound ClC1=NC=C(C=O)C(C=2C=CC=CC=2)=C1C=O PLVSCDNPHXSGGB-UHFFFAOYSA-N 0.000 description 1
- QJRPRWPHJDZDSD-UHFFFAOYSA-N 2-chloro-4-phenylpyridine-3-carbaldehyde Chemical compound ClC1=NC=CC(C=2C=CC=CC=2)=C1C=O QJRPRWPHJDZDSD-UHFFFAOYSA-N 0.000 description 1
- BEHHMVHDDBCPNL-UHFFFAOYSA-N 2-chloro-5-formyl-4-phenylpyridine-3-carbonitrile Chemical compound ClC1=NC=C(C=O)C(C=2C=CC=CC=2)=C1C#N BEHHMVHDDBCPNL-UHFFFAOYSA-N 0.000 description 1
- CUERXIYIETURCW-UHFFFAOYSA-N 2-chloro-5-formyl-4-thiophen-2-ylpyridine-3-carbonitrile Chemical compound ClC1=NC=C(C=O)C(C=2SC=CC=2)=C1C#N CUERXIYIETURCW-UHFFFAOYSA-N 0.000 description 1
- HYGVPOXUCYEPGX-UHFFFAOYSA-N 2-chloro-5-formylpyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC(C=O)=CN=C1Cl HYGVPOXUCYEPGX-UHFFFAOYSA-N 0.000 description 1
- QBFNWWRKCSBZHD-UHFFFAOYSA-N 2-chloro-5-phenylpyridine-3-carbaldehyde Chemical compound C1=C(C=O)C(Cl)=NC=C1C1=CC=CC=C1 QBFNWWRKCSBZHD-UHFFFAOYSA-N 0.000 description 1
- GRDUBKISDOCKBX-UHFFFAOYSA-N 2-chlorobut-3-enenitrile Chemical compound C=CC(Cl)C#N GRDUBKISDOCKBX-UHFFFAOYSA-N 0.000 description 1
- WTDNWEITCUMXGW-UHFFFAOYSA-N 2-chlorobutanenitrile Chemical compound CCC(Cl)C#N WTDNWEITCUMXGW-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KHPAGGHFIDLUMB-UHFFFAOYSA-N 2-chloropyridine-3-carbaldehyde Chemical compound ClC1=NC=CC=C1C=O KHPAGGHFIDLUMB-UHFFFAOYSA-N 0.000 description 1
- SAADORAEBXDJQA-UHFFFAOYSA-N 2-cyanobut-2-enoic acid Chemical compound CC=C(C#N)C(O)=O SAADORAEBXDJQA-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OLUOHHXYBBNVPD-UHFFFAOYSA-N 3-chlorobut-3-enenitrile Chemical compound ClC(=C)CC#N OLUOHHXYBBNVPD-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XGPTYHBHYLTJKC-UHFFFAOYSA-N 4,6-dichloro-5-phenylpyridine-3-carbaldehyde Chemical compound ClC1=NC=C(C=O)C(Cl)=C1C1=CC=CC=C1 XGPTYHBHYLTJKC-UHFFFAOYSA-N 0.000 description 1
- AKYJFAHYRMPRDS-UHFFFAOYSA-N 4,6-dichloropyridine-3-carbaldehyde Chemical compound ClC1=CC(Cl)=C(C=O)C=N1 AKYJFAHYRMPRDS-UHFFFAOYSA-N 0.000 description 1
- TVATXSHJPUWJHZ-UHFFFAOYSA-N 4-chlorobut-2-enenitrile Chemical compound ClCC=CC#N TVATXSHJPUWJHZ-UHFFFAOYSA-N 0.000 description 1
- NCWSGIDTDBAQAA-UHFFFAOYSA-N 4-chlorobut-3-enenitrile Chemical compound ClC=CCC#N NCWSGIDTDBAQAA-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- MZTSMFMGZMDYGL-UHFFFAOYSA-N 5-chloropent-3-enenitrile Chemical compound ClCC=CCC#N MZTSMFMGZMDYGL-UHFFFAOYSA-N 0.000 description 1
- DFHVYOSHIFFFGL-UHFFFAOYSA-N 5-formyl-N,N-dimethyl-2H-pyridine-1-carboxamide Chemical compound CN(C(=O)N1CC=CC(=C1)C=O)C DFHVYOSHIFFFGL-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- DZGDAGLYKGRTIQ-UHFFFAOYSA-N 6-chloro-4-phenylpyridine-3-carbaldehyde Chemical compound C1=NC(Cl)=CC(C=2C=CC=CC=2)=C1C=O DZGDAGLYKGRTIQ-UHFFFAOYSA-N 0.000 description 1
- JSIHSCCXRSXFOF-UHFFFAOYSA-N 6-chloro-5-hydroxypyridine-3-carbaldehyde Chemical compound OC1=CC(C=O)=CN=C1Cl JSIHSCCXRSXFOF-UHFFFAOYSA-N 0.000 description 1
- AFWWKZCPPRPDQK-UHFFFAOYSA-N 6-chloropyridine-3-carbaldehyde Chemical compound ClC1=CC=C(C=O)C=N1 AFWWKZCPPRPDQK-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IWJMQXOBCQTQCF-UHFFFAOYSA-N but-3-enal Chemical compound C=CCC=O IWJMQXOBCQTQCF-UHFFFAOYSA-N 0.000 description 1
- ZGJLJEMLZMXNFD-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=[CH] ZGJLJEMLZMXNFD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D213/82—Amides; Imides in position 3
-
- 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
- C07D213/84—Nitriles
-
- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4429465A DE4429465A1 (de) | 1994-08-19 | 1994-08-19 | Verfahren zur Herstellung von 2-Halogenpyridinaldehyden und neue 2-Halogenpyridinaldehyde |
| DE4429465.4 | 1994-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0859619A true JPH0859619A (ja) | 1996-03-05 |
Family
ID=6526101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7229616A Pending JPH0859619A (ja) | 1994-08-19 | 1995-08-16 | ２−ハロゲノピリジンアルデヒド類の製造方法および新規な２−ハロゲノピリジンアルデヒド類 |
Country Status (6)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6737529B2 (en) * | 2002-03-07 | 2004-05-18 | Council Of Scientific And Industrial Research | Process for the preparation of 2-chloro-5-methylpyridine-3-carbaldehyde |
| US6479664B1 (en) | 2002-03-18 | 2002-11-12 | Council Of Scientific And Industrial Research | Process for the preparation of 2-chloro-5-methylpyridine-3-carbaldehyde |
| EP1346984B1 (en) * | 2002-03-20 | 2008-08-06 | Council of Scientific and Industrial Research | Process for the preparation of 2-chloro-5-methylpyridine-3- carbaldehyde |
| DE102006033572A1 (de) | 2006-07-20 | 2008-01-24 | Bayer Cropscience Ag | N'-Cyano-N-halogenalkyl-imidamid Derivate |
| EP2069336B1 (en) | 2006-09-07 | 2012-12-26 | Actelion Pharmaceuticals Ltd. | Pyridin-4-yl derivatives as immunomodulating agents |
| WO2008029370A1 (en) | 2006-09-08 | 2008-03-13 | Actelion Pharmaceuticals Ltd | Pyridin-3-yl derivatives as immunomodulating agents |
| EP2125797B1 (en) | 2007-03-16 | 2014-01-15 | Actelion Pharmaceuticals Ltd. | Amino- pyridine derivatives as s1p1 /edg1 receptor agonists |
| WO2009109906A1 (en) * | 2008-03-06 | 2009-09-11 | Actelion Pharmaceuticals Ltd | Pyridine compounds |
| US8575200B2 (en) | 2008-03-07 | 2013-11-05 | Actelion Pharmaceuticals Ltd | Pyridin-2-yl derivatives as immunomodulating agents |
| SG178042A1 (en) | 2009-07-16 | 2012-03-29 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives |
| MX350009B (es) | 2011-01-19 | 2017-08-23 | Idorsia Pharmaceuticals Ltd | Derivados de 2-metoxi-piridin-4-ilo. |
| US20140113824A1 (en) | 2011-05-10 | 2014-04-24 | Bayer Intellectual Property Gmbh | Bicyclic (thio)carbonylamidines |
| HRP20200001T1 (hr) | 2015-05-20 | 2020-03-20 | Idorsia Pharmaceuticals Ltd | Kristalični oblik spoja (s)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024332A (en) * | 1973-06-05 | 1977-05-17 | Pfizer Inc. | Aminoglycoside antibiotics and intermediates therefor |
| DE2862491D1 (en) | 1977-08-12 | 1988-05-05 | Ici Plc | Trihalomethylpyridine compounds |
| US4279913A (en) | 1978-01-04 | 1981-07-21 | Merck & Co., Inc. | Polysubstituted-2-(3-loweralkylamino-2-R1 O-propoxy)pyridines |
| DE3314196A1 (de) | 1982-07-16 | 1983-09-29 | CIBA-GEIGY AG, 4002 Basel | Heterocyclylaether |
| ATE67493T1 (de) | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
| US5001138B1 (en) * | 1985-02-04 | 1998-01-20 | Bayer Agrochem Kk | Heterocyclic compounds |
| US4757073A (en) | 1986-09-30 | 1988-07-12 | Bristol-Myers Company | Antipsychotic cyclic imide derivatives of 2-(4-butylipiperazin-1-yl) pyridines, compositions and use |
| WO1992022203A1 (en) * | 1991-06-12 | 1992-12-23 | E.I. Du Pont De Nemours And Company | Substituted pyridine herbicides |
| JPH0517475A (ja) | 1991-07-09 | 1993-01-26 | Sapporo Breweries Ltd | 新規な３，４−ジヒドロ−１，８−ナフチリジン誘導体及びそれを含有する抗気管支喘息薬 |
| US5508410A (en) * | 1993-11-30 | 1996-04-16 | Reilly Industries, Inc. | Process for preparing 2-halo-5-substituted pyridines |
-
1994
- 1994-08-19 DE DE4429465A patent/DE4429465A1/de not_active Withdrawn
-
1995
- 1995-08-08 ES ES95112442T patent/ES2118481T3/es not_active Expired - Lifetime
- 1995-08-08 DE DE59502572T patent/DE59502572D1/de not_active Expired - Fee Related
- 1995-08-08 EP EP95112442A patent/EP0702003B1/de not_active Expired - Lifetime
- 1995-08-16 CA CA002156230A patent/CA2156230A1/en not_active Abandoned
- 1995-08-16 JP JP7229616A patent/JPH0859619A/ja active Pending
-
1996
- 1996-11-27 US US08/758,625 patent/US5708180A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2156230A1 (en) | 1996-02-20 |
| DE4429465A1 (de) | 1996-02-22 |
| ES2118481T3 (es) | 1998-09-16 |
| US5708180A (en) | 1998-01-13 |
| EP0702003A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-03-27 |
| EP0702003A2 (de) | 1996-03-20 |
| DE59502572D1 (de) | 1998-07-23 |
| EP0702003B1 (de) | 1998-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0859619A (ja) | ２−ハロゲノピリジンアルデヒド類の製造方法および新規な２−ハロゲノピリジンアルデヒド類 | |
| CA2729697A1 (en) | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines | |
| US6008363A (en) | Process for producing guanidine derivatives, intermediates therefor and their production | |
| US5053516A (en) | Synthesis of 2-substituted-5-methylpyridines from methylcyclobutanecarbonitrile, valeronitrile and pentenonitrile intermediates | |
| JP2806998B2 (ja) | 置換された‐２‐クロロ‐ピリジン類の製造方法 | |
| NO172341B (no) | Triprolidin-mellomprodukter | |
| US5414122A (en) | Process for producing alpha-ketoamide derivative | |
| JP3100168B2 (ja) | 置換２−クロロピリジンの製法 | |
| JPH0565272A (ja) | ２，３−ジフルオロ−５−（トリフルオロメチル）ピリジン | |
| Zhou et al. | Samarium (II) iodide induced reductive coupling of nitriles with nitro compounds | |
| CZ283077B6 (cs) | Způsob přípravy dialkyl-2,3-pyridindikarboxylátu a jeho derivátů z alfa,beta-nenasyceného oximu a aminobutendioátu | |
| EP0933362B1 (en) | A process for the preparation of pyridine dicarboxylate derivatives | |
| JP3413632B2 (ja) | グアニジン誘導体の製造方法 | |
| JPH01224364A (ja) | 除草性ｏ―カルボキシアリ―ルイミダゾリノン類の製法 | |
| HU199798B (en) | Process for producing 2-substituted-5-methyl-pyridine derivatives | |
| AU600838B2 (en) | Process for the preparation of dextrorotatory 3-(3-pyridyl)-1H, 3H-pyrrolo(1,2-c)-7-thiazolecarboxylic acid | |
| JP3253245B2 (ja) | グアニジン誘導体の製造法、新規中間体およびその製造法 | |
| JPS58116475A (ja) | １，２，４―トリアゾリウム・ベタイン化合物およびその製法 | |
| JPH0338263B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0360825B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JP2000080082A (ja) | ５−ハロゲノ−２−置換ピリジンの製造方法 | |
| JP2524544B2 (ja) | 光学活性な置換フェノキシアルカン酸アミド類の製造方法 | |
| JPH0234352B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH04139170A (ja) | 置換ピリジンスルホニルカーバメート系化合物及びその製造方法並びに置換ピリジンスルホンアミド系化合物の製造方法 | |
| US4251663A (en) | Thiosubstituted pyridines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060815 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20060824 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20070130 |