DD290190A5 - Verfahren zum herstellen von phthalazinessigsaeureestr-derivaten und einer neuen zwischenverbindung - Google Patents

Verfahren zum herstellen von phthalazinessigsaeureestr-derivaten und einer neuen zwischenverbindung Download PDF

Info

Publication number: DD290190A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; formula; solvent; oxo; compound
Prior art date: 1988-02-29

Application number

DD89326089A

Other languages

German (de)

English (en)

Inventor

Gene Sinay Terry Jr

Rober J Sysko

Original Assignee

��@��Kk��

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.)

1988-02-29

Filing date

1989-02-28

Publication date

1991-05-23

1989-02-28 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1991-05-23 Publication of DD290190A5 publication Critical patent/DD290190A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 30
238000000034 method Methods 0.000 title claims description 30
238000004519 manufacturing process Methods 0.000 title abstract description 11
230000002378 acidificating effect Effects 0.000 title 1
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 32
238000002360 preparation method Methods 0.000 claims abstract description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
239000011541 reaction mixture Substances 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 2
238000004090 dissolution Methods 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 16
235000011054 acetic acid Nutrition 0.000 abstract description 8
125000000623 heterocyclic group Chemical group 0.000 abstract description 5
-1 phthalazineacetic acid ester Chemical class 0.000 abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
150000001243 acetic acids Chemical class 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
239000007787 solid Substances 0.000 description 23
ZEDQLIHBPGNGEC-UHFFFAOYSA-N 2-(4-oxo-3h-phthalazin-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=NNC(=O)C2=C1 ZEDQLIHBPGNGEC-UHFFFAOYSA-N 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 10
ZEGOKABDRQXNOG-UHFFFAOYSA-N 2-(1-hydrazinyl-4-oxo-2,3-dihydrophthalazin-1-yl)acetic acid Chemical compound C1=CC=C2C(NN)(CC(O)=O)NNC(=O)C2=C1 ZEGOKABDRQXNOG-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 7
XKMGDVJBAWUUDZ-YVMONPNESA-N (2z)-2-(3-oxo-2-benzofuran-1-ylidene)acetic acid Chemical compound C1=CC=C2C(=C/C(=O)O)/OC(=O)C2=C1 XKMGDVJBAWUUDZ-YVMONPNESA-N 0.000 description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
239000002002 slurry Substances 0.000 description 6
239000008247 solid mixture Substances 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
125000003158 alcohol group Chemical group 0.000 description 5
238000005469 granulation Methods 0.000 description 5
230000003179 granulation Effects 0.000 description 5
LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
235000011056 potassium acetate Nutrition 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RIIVBOIBIOLLPO-UHFFFAOYSA-N 2-phthalazin-1-ylacetic acid Chemical class C1=CC=C2C(CC(=O)O)=NN=CC2=C1 RIIVBOIBIOLLPO-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000651 prodrug Chemical group 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
MRQWEYGQXMCVLY-UHFFFAOYSA-N 2-(3H-2-benzofuran-1-ylidene)acetic acid Chemical compound C1(OCC2=CC=CC=C12)=CC(=O)O MRQWEYGQXMCVLY-UHFFFAOYSA-N 0.000 description 1
OLPXAVJPVMMDQO-UHFFFAOYSA-N 2-oxo-2-phthalazin-1-ylacetic acid Chemical compound C1=CC=C2C(C(=O)C(=O)O)=NN=CC2=C1 OLPXAVJPVMMDQO-UHFFFAOYSA-N 0.000 description 1
QRNVHFPDZAZUGX-UHFFFAOYSA-N 4-methyl-2h-phthalazin-1-one Chemical compound C1=CC=C2C(C)=NNC(=O)C2=C1 QRNVHFPDZAZUGX-UHFFFAOYSA-N 0.000 description 1
241000208140 Acer Species 0.000 description 1
102000016912 Aldehyde Reductase Human genes 0.000 description 1
108010053754 Aldehyde reductase Proteins 0.000 description 1
ZRXMRFJXROONDF-UHFFFAOYSA-N C1C(=CC(=O)O)C2=CC=CC=C2O1 Chemical compound C1C(=CC(=O)O)C2=CC=CC=C2O1 ZRXMRFJXROONDF-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000009838 combustion analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Separation Of Suspended Particles By Flocculating Agents (AREA)
Furan Compounds (AREA)
Steroid Compounds (AREA)

DD89326089A 1988-02-29 1989-02-28 Verfahren zum herstellen von phthalazinessigsaeureestr-derivaten und einer neuen zwischenverbindung DD290190A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/161,540 US4904782A (en)	1988-02-29	1988-02-29	Process for the production of phthalazineacetic acid ester derivatives and a novel intermediate

Publications (1)

Publication Number	Publication Date
DD290190A5 true DD290190A5 (de)	1991-05-23

Family

ID=22581597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89326089A DD290190A5 (de)	1988-02-29	1989-02-28	Verfahren zum herstellen von phthalazinessigsaeureestr-derivaten und einer neuen zwischenverbindung

Country Status (26)

Country	Link
US (1)	US4904782A (da)
EP (1)	EP0331314B1 (da)
JP (1)	JPH029867A (da)
KR (1)	KR910000664B1 (da)
CN (1)	CN1021222C (da)
AT (1)	ATE103904T1 (da)
AU (1)	AU610347B2 (da)
CA (1)	CA1308412C (da)
DD (1)	DD290190A5 (da)
DE (1)	DE68914309T2 (da)
DK (1)	DK93089A (da)
EG (1)	EG18597A (da)
FI (1)	FI890929A7 (da)
HU (1)	HU202845B (da)
IE (1)	IE890643L (da)
IL (1)	IL89360A (da)
MX (1)	MX15078A (da)
MY (1)	MY104951A (da)
NO (1)	NO890815L (da)
NZ (1)	NZ228142A (da)
PL (4)	PL159836B1 (da)
PT (1)	PT89871B (da)
RU (1)	RU1830066C (da)
SU (3)	SU1757465A3 (da)
YU (1)	YU47207B (da)
ZA (1)	ZA891486B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991009019A1 (en) *	1989-12-15	1991-06-27	Pfizer Inc.	Substituted oxophthalazinyl acetic acids and analogs thereof
EP0982306A3 (en) *	1998-08-21	2000-07-05	Pfizer Products Inc.	Polymorph of zopolrestat monohydrate
CN116970317B (zh) *	2023-03-20	2024-06-25	安徽庆丰涂料科技有限公司	可呼吸的负离子抗菌涂料及其加工工艺

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE47592B1 (en) *	1977-12-29	1984-05-02	Ici Ltd	Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture
CA1143733A (en) *	1979-07-31	1983-03-29	Masao Yoshida	Producing 7-alkoxycarbonyl-6,8-dimethyl-4- hydroxymethyl-1-phthalazone and intermediates
IL80475A (en) *	1985-11-07	1993-01-31	Pfizer	Heterocyclic-substituted 4-oxo (or thio)-3h- phthalazinyl-acetic acid derivatives and pharmaceutical compositions containing them
JPH0676391B2 (ja) *	1987-06-09	1994-09-28	フアイザー・インコーポレイテツド	ベンゾチアゾール等の複素環側鎖を有するオキソフタラジニル酢酸類の製造方法

1988
- 1988-02-29 US US07/161,540 patent/US4904782A/en not_active Expired - Fee Related
1989
- 1989-02-16 DE DE68914309T patent/DE68914309T2/de not_active Expired - Fee Related
- 1989-02-16 AT AT89301520T patent/ATE103904T1/de not_active IP Right Cessation
- 1989-02-16 EP EP89301520A patent/EP0331314B1/en not_active Expired - Lifetime
- 1989-02-21 MY MYPI89000209A patent/MY104951A/en unknown
- 1989-02-21 IL IL8936089A patent/IL89360A/en not_active IP Right Cessation
- 1989-02-23 EG EG96/89A patent/EG18597A/xx active
- 1989-02-24 PL PL1989293141A patent/PL159836B1/pl unknown
- 1989-02-24 CA CA000591998A patent/CA1308412C/en not_active Expired - Lifetime
- 1989-02-24 PL PL1989293143A patent/PL160288B1/pl unknown
- 1989-02-24 PL PL1989293142A patent/PL159837B1/pl unknown
- 1989-02-24 PL PL1989277923A patent/PL159784B1/pl unknown
- 1989-02-27 MX MX1507889A patent/MX15078A/es unknown
- 1989-02-27 SU SU894613499A patent/SU1757465A3/ru active
- 1989-02-27 JP JP1046349A patent/JPH029867A/ja active Pending
- 1989-02-27 NZ NZ228142A patent/NZ228142A/en unknown
- 1989-02-27 AU AU30772/89A patent/AU610347B2/en not_active Ceased
- 1989-02-27 FI FI890929A patent/FI890929A7/fi not_active Application Discontinuation
- 1989-02-27 NO NO89890815A patent/NO890815L/no unknown
- 1989-02-27 YU YU42489A patent/YU47207B/sh unknown
- 1989-02-27 ZA ZA891486A patent/ZA891486B/xx unknown
- 1989-02-27 DK DK093089A patent/DK93089A/da not_active Application Discontinuation
- 1989-02-27 CN CN89100944A patent/CN1021222C/zh not_active Expired - Fee Related
- 1989-02-28 DD DD89326089A patent/DD290190A5/de not_active IP Right Cessation
- 1989-02-28 IE IE890643A patent/IE890643L/xx unknown
- 1989-02-28 HU HU89931A patent/HU202845B/hu not_active IP Right Cessation
- 1989-02-28 PT PT89871A patent/PT89871B/pt not_active IP Right Cessation
- 1989-02-28 KR KR1019890002510A patent/KR910000664B1/ko not_active Expired
- 1989-10-20 SU SU894742185A patent/SU1736340A3/ru active
- 1989-10-20 RU SU894742282A patent/RU1830066C/ru active
- 1989-10-20 SU SU894742177A patent/SU1766256A3/ru active

Also Published As

Publication number	Publication date
PL277923A1 (en)	1989-09-04
FI890929A0 (fi)	1989-02-27
CN1036953A (zh)	1989-11-08
RU1830066C (ru)	1993-07-23
NZ228142A (en)	1990-10-26
US4904782A (en)	1990-02-27
HUT51259A (en)	1990-04-28
KR890012975A (ko)	1989-09-20
EP0331314A2 (en)	1989-09-06
PT89871A (pt)	1989-10-04
MY104951A (en)	1994-07-30
YU47207B (sh)	1995-01-31
DE68914309T2 (de)	1994-07-14
IE890643L (en)	1989-08-29
PL159784B1 (en)	1993-01-29
DK93089D0 (da)	1989-02-27
JPH029867A (ja)	1990-01-12
DK93089A (da)	1989-08-30
HU202845B (en)	1991-04-29
PL160288B1 (pl)	1993-02-26
AU610347B2 (en)	1991-05-16
IL89360A0 (en)	1989-09-10
EG18597A (en)	1993-08-30
CA1308412C (en)	1992-10-06
EP0331314A3 (en)	1991-06-12
PL159836B1 (pl)	1993-01-29
SU1736340A3 (ru)	1992-05-23
AU3077289A (en)	1989-08-31
ZA891486B (en)	1990-10-31
IL89360A (en)	1994-08-26
NO890815L (no)	1989-08-30
MX15078A (es)	1993-05-01
SU1766256A3 (ru)	1992-09-30
YU42489A (en)	1990-12-31
PL159837B1 (pl)	1993-01-29
PT89871B (pt)	1994-04-29
CN1021222C (zh)	1993-06-16
NO890815D0 (no)	1989-02-27
KR910000664B1 (ko)	1991-01-31
FI890929A7 (fi)	1989-08-30
ATE103904T1 (de)	1994-04-15
EP0331314B1 (en)	1994-04-06
DE68914309D1 (de)	1994-05-11
SU1757465A3 (ru)	1992-08-23

Legal Events

Date	Code	Title	Description
1996-06-20	ENJ	Ceased due to non-payment of renewal fee

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