BG109230A - Метод за получаване на 3-[2-(3,4-диметокси-бензоил)-4,5-диметокси-фенил]-пентан-2-он - Google Patents

Метод за получаване на 3-[2-(3,4-диметокси-бензоил)-4,5-диметокси-фенил]-пентан-2-он Download PDF

Info

Publication number: BG109230A
Authority: BG; Bulgaria
Prior art keywords: compound; general formula; dimethoxy; alkali; involves
Prior art date: 2002-12-16

Application number

BG109230A

Other languages

Bulgarian (bg)

English (en)

Inventor

Samu Erika Molnarne

Gyula Simig

Original Assignee

Egis Gyogyszergyar Rt.

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.)

2002-12-16

Filing date

2005-07-14

Publication date

2006-04-28

2005-07-14 Application filed by Egis Gyogyszergyar Rt. filed Critical Egis Gyogyszergyar Rt.

2006-04-28 Publication of BG109230A publication Critical patent/BG109230A/bg

Links

238000000034 method Methods 0.000 title claims abstract description 36
238000002360 preparation method Methods 0.000 title claims abstract description 14
ZWUMDFWFKWDFBI-UHFFFAOYSA-N 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1C(=O)C1=CC=C(OC)C(OC)=C1 ZWUMDFWFKWDFBI-UHFFFAOYSA-N 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 55
-1 3,4-dimethoxy-benzoyl Chemical group 0.000 claims description 23
239000003513 alkali Substances 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 17
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
150000002681 magnesium compounds Chemical class 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
239000005977 Ethylene Substances 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
238000006467 substitution reaction Methods 0.000 claims description 5
230000003301 hydrolyzing effect Effects 0.000 claims description 4
CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
150000002641 lithium Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000002253 acid Substances 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000003993 interaction Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
BLWGLUGFLOPVHX-UHFFFAOYSA-N 3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1Br BLWGLUGFLOPVHX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000002642 lithium compounds Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
RUEQJZPDBYLHPF-UHFFFAOYSA-N 3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one;ethene Chemical group C=C.CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1Br RUEQJZPDBYLHPF-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
229910052794 bromium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
150000001844 chromium Chemical class 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
BIGQPYZPEWAPBG-UHFFFAOYSA-N methyl 3,4-dimethoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(OC)=C1 BIGQPYZPEWAPBG-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 1
SOJNQJRJHNNHHG-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)pentan-2-one Chemical compound CCC(C(C)=O)C1=CC=C(OC)C(OC)=C1 SOJNQJRJHNNHHG-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
125000006416 CBr Chemical group BrC* 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
238000003747 Grignard reaction Methods 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
239000005909 Kieselgur Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 1
KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical group [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
JBJSGZSKYIDCQR-UHFFFAOYSA-N ethene;pentan-2-one Chemical group C=C.CCCC(C)=O JBJSGZSKYIDCQR-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960002501 tofisopam Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BG109230A 2002-12-16 2005-07-14 Метод за получаване на 3-[2-(3,4-диметокси-бензоил)-4,5-диметокси-фенил]-пентан-2-он BG109230A (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU0204342A HU227044B1 (en)	2002-12-16	2002-12-16	Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one

Publications (1)

Publication Number	Publication Date
BG109230A true BG109230A (bg)	2006-04-28

Family

ID=89981000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG109230A BG109230A (bg)	2002-12-16	2005-07-14	Метод за получаване на 3-[2-(3,4-диметокси-бензоил)-4,5-диметокси-фенил]-пентан-2-он

Country Status (12)

Country	Link
EP (1)	EP1575890A1 (pl)
JP (1)	JP4437093B2 (pl)
KR (1)	KR100936306B1 (pl)
AU (2)	AU2002361068A1 (pl)
BG (1)	BG109230A (pl)
CZ (1)	CZ2005388A3 (pl)
EA (1)	EA007788B1 (pl)
HU (1)	HU227044B1 (pl)
PL (1)	PL376530A1 (pl)
SK (1)	SK702005A3 (pl)
UA (1)	UA78634C2 (pl)
WO (2)	WO2004054951A1 (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100714181B1 (ko) *	2005-07-04	2007-05-04	주식회사 자동기	제설재 살포기용 연료공급장치
CN104098482B (zh) *	2013-04-12	2016-04-20	江苏英力科技发展有限公司	一种3,4-二甲氧基-n,n-二甲基苯甲酰胺的制备方法
CN104262128B (zh) *	2014-09-04	2016-04-13	山东金城医药化工股份有限公司	托非索泮中间体的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU194529B (en) *	1984-07-20	1988-02-29	Gyogyszerkutato Intezet	New process for producing 2-aroyl-phenylacetone-derivatives
SK2792004A3 (en) *	2001-12-13	2004-11-03	Egyt Gyogyszervegyeszeti Gyar	Process for the preparation of tofisopam and new intermediates

2002
- 2002-12-16 HU HU0204342A patent/HU227044B1/hu not_active IP Right Cessation
- 2002-12-31 KR KR1020057011012A patent/KR100936306B1/ko not_active Expired - Fee Related
- 2002-12-31 SK SK70-2005A patent/SK702005A3/sk unknown
- 2002-12-31 EP EP02791921A patent/EP1575890A1/en not_active Withdrawn
- 2002-12-31 CZ CZ2005388A patent/CZ2005388A3/cs unknown
- 2002-12-31 AU AU2002361068A patent/AU2002361068A1/en not_active Abandoned
- 2002-12-31 JP JP2004559931A patent/JP4437093B2/ja not_active Expired - Fee Related
- 2002-12-31 EA EA200500966A patent/EA007788B1/ru not_active IP Right Cessation
- 2002-12-31 PL PL376530A patent/PL376530A1/pl not_active IP Right Cessation
- 2002-12-31 UA UAA200507059A patent/UA78634C2/uk unknown
- 2002-12-31 WO PCT/HU2002/000178 patent/WO2004054951A1/en not_active Ceased
2003
- 2003-12-16 AU AU2003292449A patent/AU2003292449A1/en not_active Abandoned
- 2003-12-16 WO PCT/HU2003/000104 patent/WO2004054952A1/en not_active Ceased
2005
- 2005-07-14 BG BG109230A patent/BG109230A/bg unknown

Also Published As

Publication number	Publication date
HUP0204342A3 (en)	2004-11-29
WO2004054951A1 (en)	2004-07-01
AU2003292449A1 (en)	2004-07-09
UA78634C2 (en)	2007-04-10
CZ2005388A3 (cs)	2005-09-14
EP1575890A1 (en)	2005-09-21
WO2004054952A1 (en)	2004-07-01
HUP0204342A2 (hu)	2004-07-28
EA007788B1 (ru)	2007-02-27
PL376530A1 (pl)	2006-01-09
SK702005A3 (sk)	2005-09-08
KR20050085686A (ko)	2005-08-29
HU227044B1 (en)	2010-05-28
JP2006509814A (ja)	2006-03-23
HU0204342D0 (en)	2003-02-28
KR100936306B1 (ko)	2010-01-12
JP4437093B2 (ja)	2010-03-24
EA200500966A1 (ru)	2005-12-29
AU2002361068A1 (en)	2004-07-09

Publication	Publication Date	Title
CZ282922B6 (cs)	1997-11-12	Způsob syntézy (4R-cis)-1,1-dimethylethyl-6-kyanomethyl-2,2-dimethyl-1,3-dioxan-4-acetátu a meziprodukty pro tento způsob
JPS5834474B2 (ja)	1983-07-27	チアゾリジン誘導体の製造法
EP0605392B1 (en)	1997-04-09	Process for producing methoxyminoacetamide compounds
JP3850838B2 (ja)	2006-11-29	トランス−４−アミノ−１−シクロヘキサンカルボン酸誘導体の製造方法
HU187816B (en)	1986-02-28	Process for producing cepheme-carboxylic acid derivatives
EP2975021B1 (en)	2017-07-26	Process for the preparation of iopamidol
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WO2009084827A2 (en)	2009-07-09	Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom
KR100936306B1 (ko)	2010-01-12	3-[2-(3,4-다이메톡시-벤조일)-4,5-다이메톡시-페닐]-펜탄-2-온의 제조 방법
KR100540148B1 (ko)	2005-12-29	에틸（2）-（메톡시이미노）（2-＜［（〈（１ｅ）-1-［3-（트리플루오로메틸）페닐］-에틸리덴〉아미노）옥시］메틸＞페닐）아세테이트 또는 에틸（2）-（메톡시이미노）＜2-［（〈［（１ｅ）-（4-클로로페닐）（시클로프로필）-메틸렌］아미노〉옥시）메틸］페닐＞아세테이트
US5696271A (en)	1997-12-09	Process for the preparation of 3-isoxazolecarboxylic acid
US2948725A (en)	1960-08-09	Flow sheet-process
US5066825A (en)	1991-11-19	Process for preparing a naphthalene derivative
HU187822B (en)	1986-02-28	Process for producing tetra-substituted cyclopropane derivatives
US4316037A (en)	1982-02-16	N-Benzyl and N-substituted benzyl tetrazole-5-carboxylic acids and the preparation thereof
JP4371054B2 (ja)	2009-11-25	キノリンカルバルデヒド類の製造方法
JPWO2006080339A1 (ja)	2008-06-19	５−クロロ−２，４−ジヒドロキシピリジンの製造方法
JP2815988B2 (ja)	1998-10-27	３―ｎ―シクロヘキシルアミノフェノール誘導体の製造法
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