UA77478C2 - A process for the preparation of [1,4,5]-oxadiazepine derivatives - Google Patents

A process for the preparation of [1,4,5]-oxadiazepine derivatives Download PDF

Info

Publication number: UA77478C2
Authority: UA; Ukraine
Prior art keywords: oxadiazepine; solvent; reaction; temperature; preparation
Prior art date: 2001-12-18

Application number

UA20040705883A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Syngenta Participations Ag

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.)

2001-12-18

Filing date

2002-12-17

Publication date

2006-12-15

2002-12-17 Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag

2006-12-15 Publication of UA77478C2 publication Critical patent/UA77478C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title abstract description 12
NNHCFSLBNPIGQO-UHFFFAOYSA-N 1,4,5-oxadiazepine Chemical class O1C=CN=NC=C1 NNHCFSLBNPIGQO-UHFFFAOYSA-N 0.000 title abstract description 3
238000006243 chemical reaction Methods 0.000 claims abstract description 25
239000002253 acid Substances 0.000 claims abstract description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
RYDICHIKLKVOEJ-UHFFFAOYSA-N oxadiazepine Chemical class O1C=CC=CN=N1 RYDICHIKLKVOEJ-UHFFFAOYSA-N 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 15
239000002798 polar solvent Substances 0.000 claims description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
230000003993 interaction Effects 0.000 claims description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
238000012876 topography Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
239000000203 mixture Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
-1 Alkyl radicals Chemical class 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000010438 heat treatment Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000000047 product Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000005037 alkyl phenyl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000005059 halophenyl group Chemical group 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000005036 alkoxyphenyl group Chemical group 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
CYMJPJKHCSDSRG-UHFFFAOYSA-N pyrazolidine-3,4-dione Chemical compound O=C1CNNC1=O CYMJPJKHCSDSRG-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
CYGBSMOHJPEUEV-UHFFFAOYSA-N 1,4,5-oxadiazepine;hydrochloride Chemical compound Cl.O1C=CN=NC=C1 CYGBSMOHJPEUEV-UHFFFAOYSA-N 0.000 description 1
JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000006307 alkoxy benzyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000006177 alkyl benzyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
230000015572 biosynthetic process Effects 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000007872 degassing Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000006277 halobenzyl group Chemical group 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000009434 installation Methods 0.000 description 1
230000016507 interphase Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
IMTXVUJCYIUNHT-UHFFFAOYSA-N oxadiazepine hydrochloride Chemical compound Cl.O1N=NC=CC=C1 IMTXVUJCYIUNHT-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/06—Seven-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

UA20040705883A 2001-12-18 2002-12-17 A process for the preparation of [1,4,5]-oxadiazepine derivatives UA77478C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH23132001		2001-12-18
PCT/EP2002/014414 WO2003051853A1 (en)	2001-12-18	2002-12-17	PROCESS FOR THE PREPARATION OF `1,4,5&excl;-OXADIAZEPINE DERIVATIVES

Publications (1)

Publication Number	Publication Date
UA77478C2 true UA77478C2 (en)	2006-12-15

Family

ID=4568528

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040705883A UA77478C2 (en)	2001-12-18	2002-12-17	A process for the preparation of [1,4,5]-oxadiazepine derivatives

Country Status (22)

Country	Link
US (1)	US7598376B2 (pl)
EP (1)	EP1458696B1 (pl)
JP (1)	JP2005511788A (pl)
KR (1)	KR20040072665A (pl)
CN (1)	CN1279032C (pl)
AR (2)	AR037853A1 (pl)
AT (1)	ATE374757T1 (pl)
AU (1)	AU2002366284B2 (pl)
BR (1)	BR0214956B1 (pl)
CA (1)	CA2469044A1 (pl)
DE (1)	DE60222806T2 (pl)
EA (1)	EA006511B1 (pl)
HR (1)	HRP20040654B1 (pl)
HU (1)	HU230510B1 (pl)
IL (2)	IL162188A0 (pl)
MX (1)	MXPA04005788A (pl)
PL (1)	PL207150B1 (pl)
RO (1)	RO121850B1 (pl)
TW (1)	TWI316939B (pl)
UA (1)	UA77478C2 (pl)
WO (1)	WO2003051853A1 (pl)
ZA (1)	ZA200404034B (pl)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2579742C (en) *	2004-10-27	2013-07-02	Dominik Faber	A process for the preparation of [1,4,5]-oxadiazepane derivatives
AR087008A1 (es)	2011-06-22	2014-02-05	Syngenta Participations Ag	Derivados de n-oxi-pirazolo-triazepina-diona
CN108264493B (zh) *	2016-12-30	2022-09-30	泸州东方农化有限公司	一种制备氧二氮杂环化合物的工艺及其应用
WO2018120093A1 (zh) *	2016-12-30	2018-07-05	泸州东方农化有限公司	一种制备氧二氮杂环化合物的工艺及其应用
CN107445915A (zh) *	2017-09-18	2017-12-08	张家港九力新材料科技有限公司	一种4,5‑二叔丁氧羰基‑[1,4,5]氧二氮杂庚烷制备方法
CN108017593B (zh) *	2017-12-06	2021-05-11	东南大学	一种简便高效的1-氧-4,5-二氮杂环庚烷合成方法
CN112522340B (zh) *	2019-09-19	2023-05-09	四川利尔生物科技有限公司	酶催化水解制备1-氧-4,5-二氮杂环庚烷的方法
GB202206290D0 (en)	2022-04-29	2022-06-15	Syngenta Crop Protection Ag	Process
CN117247364B (zh) *	2023-09-01	2025-07-25	北京颖泰嘉和生物科技股份有限公司	一种n,n-二乙酰基-[1,4,5]氧杂二氮氧环庚烷及其制备方法
CN117603156A (zh) *	2023-11-22	2024-02-27	浙江工业大学	一种唑啉草酯中间体n-乙酰基-[1,4,5]-氧二氮杂庚烷的合成方法
CN118184600A (zh) *	2024-03-08	2024-06-14	上海农帆生物科技有限公司	一种[1,4,5]氧二氮杂庚烷的制备方法及应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5015637A (en) *	1990-05-25	1991-05-14	Hoechst-Roussel Pharmaceutical Inc.	Pyrido[3,4-b]pyrrolo[1,2-e][1,4,5]oxadiazepines
PL356456A1 (pl) *	1999-09-07	2004-06-28	Syngenta Participations Ag	Nowe środki chwastobójcze
CA2579742C (en) *	2004-10-27	2013-07-02	Dominik Faber	A process for the preparation of [1,4,5]-oxadiazepane derivatives

2002
- 2002-12-16 AR ARP020104880A patent/AR037853A1/es active IP Right Grant
- 2002-12-16 TW TW091136243A patent/TWI316939B/zh not_active IP Right Cessation
- 2002-12-17 MX MXPA04005788A patent/MXPA04005788A/es active IP Right Grant
- 2002-12-17 PL PL369718A patent/PL207150B1/pl unknown
- 2002-12-17 HU HU0402475A patent/HU230510B1/hu unknown
- 2002-12-17 KR KR10-2004-7009662A patent/KR20040072665A/ko not_active Ceased
- 2002-12-17 JP JP2003552738A patent/JP2005511788A/ja active Pending
- 2002-12-17 DE DE60222806T patent/DE60222806T2/de not_active Expired - Lifetime
- 2002-12-17 IL IL16218802A patent/IL162188A0/xx unknown
- 2002-12-17 UA UA20040705883A patent/UA77478C2/uk unknown
- 2002-12-17 HR HR20040654A patent/HRP20040654B1/xx not_active IP Right Cessation
- 2002-12-17 US US10/498,865 patent/US7598376B2/en not_active Expired - Lifetime
- 2002-12-17 BR BRPI0214956-7A patent/BR0214956B1/pt active IP Right Grant
- 2002-12-17 CA CA002469044A patent/CA2469044A1/en not_active Abandoned
- 2002-12-17 EA EA200400739A patent/EA006511B1/ru not_active IP Right Cessation
- 2002-12-17 CN CNB028253787A patent/CN1279032C/zh not_active Expired - Lifetime
- 2002-12-17 EP EP02804910A patent/EP1458696B1/en not_active Expired - Lifetime
- 2002-12-17 AU AU2002366284A patent/AU2002366284B2/en not_active Expired
- 2002-12-17 AT AT02804910T patent/ATE374757T1/de not_active IP Right Cessation
- 2002-12-17 WO PCT/EP2002/014414 patent/WO2003051853A1/en not_active Ceased
- 2002-12-17 RO ROA200400536A patent/RO121850B1/ro unknown
2004
- 2004-05-24 ZA ZA2004/04034A patent/ZA200404034B/en unknown
- 2004-05-27 IL IL162188A patent/IL162188A/en unknown
2012
- 2012-09-21 AR ARP120103496A patent/AR087991A2/es unknown

Also Published As

Publication number	Publication date
TW200301258A (en)	2003-07-01
HUP0402475A2 (hu)	2005-03-29
MXPA04005788A (es)	2004-09-13
CA2469044A1 (en)	2003-06-26
TWI316939B (en)	2009-11-11
JP2005511788A (ja)	2005-04-28
WO2003051853A1 (en)	2003-06-26
ATE374757T1 (de)	2007-10-15
KR20040072665A (ko)	2004-08-18
DE60222806T2 (de)	2008-07-10
RO121850B1 (ro)	2008-06-30
BR0214956B1 (pt)	2012-11-27
AR037853A1 (es)	2004-12-09
CN1604896A (zh)	2005-04-06
HU230510B1 (hu)	2016-09-28
EA006511B1 (ru)	2005-12-29
AU2002366284B2 (en)	2008-10-23
HRP20040654A2 (en)	2004-12-31
AU2002366284A1 (en)	2003-06-30
DE60222806D1 (de)	2007-11-15
HUP0402475A3 (en)	2008-10-28
EA200400739A1 (ru)	2004-12-30
AR087991A2 (es)	2014-04-30
CN1279032C (zh)	2006-10-11
HRP20040654B1 (hr)	2008-07-31
PL369718A1 (pl)	2005-05-02
IL162188A0 (en)	2005-11-20
ZA200404034B (en)	2005-10-26
US20050159313A1 (en)	2005-07-21
US7598376B2 (en)	2009-10-06
EP1458696B1 (en)	2007-10-03
BR0214956A (pt)	2004-12-14
PL207150B1 (pl)	2010-11-30
IL162188A (en)	2009-05-04
EP1458696A1 (en)	2004-09-22

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