DD274213A5 - Verfahren zur herstellung von neuen 5-halogen-6-amino-nikotin-saeurehalogeniden - Google Patents

Verfahren zur herstellung von neuen 5-halogen-6-amino-nikotin-saeurehalogeniden Download PDF

Info

Publication number: DD274213A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; amino; halogen; hydrogen; halo
Prior art date: 1987-07-11

Application number

DD88317740A

Other languages

German (de)

English (en)

Inventor

Hans Lindel

Werner Hallenbach

Original Assignee

��@��k��

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.)

1987-07-11

Filing date

1988-07-08

Publication date

1989-12-13

1988-07-08 Application filed by ��@��k�� filed Critical ��@��k��

1989-12-13 Publication of DD274213A5 publication Critical patent/DD274213A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 14
239000002253 acid Substances 0.000 title claims description 3
238000000034 method Methods 0.000 title abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 7
241000251730 Chondrichthyes Species 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical class CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
150000007513 acids Chemical class 0.000 claims 1
150000002576 ketones Chemical class 0.000 abstract description 5
230000002140 halogenating effect Effects 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
-1 alkyl acetate Chemical compound 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
229960003512 nicotinic acid Drugs 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OIWWOFXSQCFZNF-UHFFFAOYSA-N 1-(6-amino-5-chloropyridin-3-yl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CN=C(N)C(Cl)=C1 OIWWOFXSQCFZNF-UHFFFAOYSA-N 0.000 description 1
YXIDFAIEDQBXMT-UHFFFAOYSA-N 1-(6-amino-5-chloropyridin-3-yl)-2-(propan-2-ylamino)ethanone Chemical compound CC(C)NCC(=O)C1=CN=C(N)C(Cl)=C1 YXIDFAIEDQBXMT-UHFFFAOYSA-N 0.000 description 1
XXHONQJWLPIFFD-UHFFFAOYSA-N 1-(6-amino-5-chloropyridin-3-yl)-2-bromoethanone Chemical compound NC1=NC=C(C(=O)CBr)C=C1Cl XXHONQJWLPIFFD-UHFFFAOYSA-N 0.000 description 1
YQMOPPLOWPRYKU-UHFFFAOYSA-N 1-(6-amino-5-chloropyridin-3-yl)ethanone Chemical compound CC(=O)C1=CN=C(N)C(Cl)=C1 YQMOPPLOWPRYKU-UHFFFAOYSA-N 0.000 description 1
AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
RJHVFCYNRKFQHA-UHFFFAOYSA-N 5-bromo-6-(methylamino)pyridine-3-carboxylic acid Chemical compound CNC1=NC=C(C(O)=O)C=C1Br RJHVFCYNRKFQHA-UHFFFAOYSA-N 0.000 description 1
UOUDHTBHPQJUPS-UHFFFAOYSA-N 6-amino-5-bromopyridine-3-carboxylic acid Chemical compound NC1=NC=C(C(O)=O)C=C1Br UOUDHTBHPQJUPS-UHFFFAOYSA-N 0.000 description 1
ODKOPTSSZHBINK-UHFFFAOYSA-N 6-amino-5-chloropyridine-3-carboxylic acid Chemical compound NC1=NC=C(C(O)=O)C=C1Cl ODKOPTSSZHBINK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 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
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 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
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000013547 stew Nutrition 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
- C07D213/26—Radicals substituted by 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD88317740A 1987-07-11 1988-07-08 Verfahren zur herstellung von neuen 5-halogen-6-amino-nikotin-saeurehalogeniden DD274213A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873723069 DE3723069A1 (de)	1987-07-11	1987-07-11	5-halogen-6-amino-nikotinsaeurehalogenide, ihre herstellung und ihre verwendung

Publications (1)

Publication Number	Publication Date
DD274213A5 true DD274213A5 (de)	1989-12-13

Family

ID=6331447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88317740A DD274213A5 (de)	1987-07-11	1988-07-08	Verfahren zur herstellung von neuen 5-halogen-6-amino-nikotin-saeurehalogeniden

Country Status (12)

Country	Link
US (1)	US4895950A (da)
EP (1)	EP0302227B1 (da)
JP (1)	JPS6431768A (da)
KR (1)	KR890002011A (da)
AT (1)	ATE84524T1 (da)
DD (1)	DD274213A5 (da)
DE (2)	DE3723069A1 (da)
DK (1)	DK384188A (da)
ES (1)	ES2053626T3 (da)
HU (1)	HU199420B (da)
IL (1)	IL87043A (da)
ZA (1)	ZA884914B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4006794A1 (de) *	1990-03-03	1991-09-05	Bayer Ag	Verfahren zur herstellung von aminoethanolderivaten
IL111117A0 (en) *	1993-10-05	1994-11-28	Shell Int Research	Process for the preparation of acid chlorine compounds
KR100386086B1 (ko) *	2000-10-27	2003-06-02	김병수	해조류의 추출물을 이용한 건강식품 및 그의제조방법
US20100016603A1 (en) *	2007-01-29	2010-01-21	Fujifilm Finechemicals Co., Ltd.	Production process of 2,3'-bipyridyl-6'-one
WO2015097850A1 (ja) *	2013-12-27	2015-07-02	アグロカネショウ株式会社	２－アミノニコチン酸ベンジルエステル誘導体の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4129734A (en) *	1976-12-03	1978-12-12	The Dow Chemical Company	Substituted pyridine carbonyl halides and derivatives
US4596883A (en) *	1984-07-05	1986-06-24	Ppg Industries, Inc.	Herbicidally active substituted diphenyl ethers
DE3615293A1 (de) *	1986-05-06	1987-11-12	Bayer Ag	Verwendung von heteroarylethylaminen zur leistungsfoerderung bei tieren, heteroarylethylamine und verfahren zu ihrer herstellung

1987
- 1987-07-11 DE DE19873723069 patent/DE3723069A1/de not_active Withdrawn
1988
- 1988-06-30 EP EP88110464A patent/EP0302227B1/de not_active Expired - Lifetime
- 1988-06-30 ES ES88110464T patent/ES2053626T3/es not_active Expired - Lifetime
- 1988-06-30 DE DE8888110464T patent/DE3877455D1/de not_active Expired - Fee Related
- 1988-06-30 AT AT88110464T patent/ATE84524T1/de not_active IP Right Cessation
- 1988-07-04 KR KR1019880008248A patent/KR890002011A/ko not_active Ceased
- 1988-07-06 JP JP63167032A patent/JPS6431768A/ja active Pending
- 1988-07-07 US US07/216,047 patent/US4895950A/en not_active Expired - Fee Related
- 1988-07-08 HU HU883603A patent/HU199420B/hu not_active IP Right Cessation
- 1988-07-08 DD DD88317740A patent/DD274213A5/de not_active IP Right Cessation
- 1988-07-08 ZA ZA884914A patent/ZA884914B/xx unknown
- 1988-07-08 DK DK384188A patent/DK384188A/da not_active Application Discontinuation
- 1988-07-08 IL IL87043A patent/IL87043A/xx unknown

Also Published As

Publication number	Publication date
JPS6431768A (en)	1989-02-02
HUT48595A (en)	1989-06-28
EP0302227A3 (en)	1989-03-15
ES2053626T3 (es)	1994-08-01
DE3723069A1 (de)	1989-01-19
EP0302227B1 (de)	1993-01-13
EP0302227A2 (de)	1989-02-08
DK384188A (da)	1989-01-12
US4895950A (en)	1990-01-23
HU199420B (en)	1990-02-28
IL87043A (en)	1992-03-29
DK384188D0 (da)	1988-07-08
IL87043A0 (en)	1988-12-30
ATE84524T1 (de)	1993-01-15
DE3877455D1 (de)	1993-02-25
KR890002011A (ko)	1989-04-07
ZA884914B (en)	1989-03-29

Legal Events

Date	Code	Title	Description
2001-01-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3010195C2 (da)	1990-10-25
EP0606065B1 (de)	1999-08-25	Verfahren zur Herstellung von Biphenylderivaten
DD274213A5 (de)	1989-12-13	Verfahren zur herstellung von neuen 5-halogen-6-amino-nikotin-saeurehalogeniden
EP0299277B1 (de)	1995-10-18	Verfahren zur Herstellung von substituierten Pyridylalkylketonen
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