DD249479A5 - Verfahren zur herstellung von propionamidin-derivaten - Google Patents

Verfahren zur herstellung von propionamidin-derivaten Download PDF

Info

Publication number: DD249479A5
Authority: DD; German Democratic Republic
Prior art keywords: sulfamyl; guanidinothiazol; formula; propionamidine; alkylation
Prior art date: 1985-09-11

Application number

DD86294264A

Other languages

German (de)

English (en)

Inventor

Peter Bod

Kalman Harsanyi

Eva Agai

Erik Bogsch

Eva Fekecs

Ferenc Trischler

Gyoergy Domany

Istvan Szabadkai

Bela Hegedues

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.)

1985-09-11

Filing date

1986-09-09

Publication date

1987-09-09

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10963968&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD249479(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1986-09-09 Application filed by ��@��@��@��@��Kk�� filed Critical ��@��@��@��@��Kk��

1987-09-09 Publication of DD249479A5 publication Critical patent/DD249479A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 33
238000002360 preparation method Methods 0.000 title claims abstract description 8
GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical class CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 title description 2
XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 claims abstract description 20
-1 2-guanidinothiazol-4-ylmethyl Chemical group 0.000 claims abstract description 12
238000005804 alkylation reaction Methods 0.000 claims abstract description 11
238000011065 in-situ storage Methods 0.000 claims abstract description 7
230000029936 alkylation Effects 0.000 claims abstract description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
239000003637 basic solution Substances 0.000 claims description 3
229960001596 famotidine Drugs 0.000 abstract description 18
150000001875 compounds Chemical class 0.000 abstract description 7
239000000126 substance Substances 0.000 abstract description 3
230000002429 anti-coagulating effect Effects 0.000 abstract 1
230000003373 anti-fouling effect Effects 0.000 abstract 1
229960003761 propamidine Drugs 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 7
DOWMJKWFABWEAH-UHFFFAOYSA-N n'-sulfamoylprop-2-enimidamide Chemical compound NS(=O)(=O)NC(=N)C=C DOWMJKWFABWEAH-UHFFFAOYSA-N 0.000 description 7
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
AHNNULCXEIGUHA-UHFFFAOYSA-N 2-[4-(sulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(N)=NC1=NC(CS)=CS1 AHNNULCXEIGUHA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
FSKYYRZENXOYAP-UHFFFAOYSA-N 2-[4-(2-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CSCCC#N)=CS1 FSKYYRZENXOYAP-UHFFFAOYSA-N 0.000 description 2
INDWVHABTMSBCJ-UHFFFAOYSA-N 3-methylsulfanylpropanenitrile Chemical compound CSCCC#N INDWVHABTMSBCJ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
IVLQMIVEODCGLH-UHFFFAOYSA-N 3-chloro-n'-sulfamoylpropanimidamide;hydrochloride Chemical compound Cl.ClCCC(/N)=N/S(N)(=O)=O IVLQMIVEODCGLH-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical class OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
RNZYZIJPRMPMED-UHFFFAOYSA-N 3-methylsulfanyl-n'-sulfamoylpropanimidamide Chemical compound CSCCC(=N)NS(N)(=O)=O RNZYZIJPRMPMED-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
239000000051 antiandrogen Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000008021 deposition Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
ZWWPJQTUGCPRMO-UHFFFAOYSA-N methanimidoyl methanimidate Chemical compound N=COC=N ZWWPJQTUGCPRMO-UHFFFAOYSA-N 0.000 description 1
PLPIVSVTRFQJFM-UHFFFAOYSA-N methanimidoyl methanimidate;hydrochloride Chemical compound Cl.N=COC=N PLPIVSVTRFQJFM-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD86294264A 1985-09-11 1986-09-09 Verfahren zur herstellung von propionamidin-derivaten DD249479A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU853424A HU194845B (en)	1985-09-11	1985-09-11	Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin

Publications (1)

Publication Number	Publication Date
DD249479A5 true DD249479A5 (de)	1987-09-09

Family

ID=10963968

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86294264A DD249479A5 (de)	1985-09-11	1986-09-09	Verfahren zur herstellung von propionamidin-derivaten

Country Status (22)

Country	Link
US (1)	US4835281A (da)
JP (1)	JPH0645609B2 (da)
KR (1)	KR910000237B1 (da)
CN (1)	CN1013674B (da)
AR (1)	AR240319A1 (da)
AT (1)	AT386824B (da)
AU (1)	AU587279B2 (da)
BE (1)	BE905409A (da)
CA (1)	CA1263120A (da)
DD (1)	DD249479A5 (da)
DK (1)	DK169920B1 (da)
ES (1)	ES2001677A6 (da)
FI (1)	FI86423C (da)
GB (1)	GB2180237B (da)
GE (1)	GEP19960471B (da)
GR (1)	GR862308B (da)
HU (1)	HU194845B (da)
NL (1)	NL8602225A (da)
NO (1)	NO163010C (da)
PT (1)	PT83348B (da)
SE (1)	SE8603797L (da)
SU (1)	SU1450743A3 (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU194845B (en) *	1985-09-11	1988-03-28	Richter Gedeon Vegyeszet	Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin
HU196775B (en) *	1986-08-05	1989-01-30	Richter Gedeon Vegyeszet	Process for production of morfologically unique new modifications of famotidin and medical compositions containing such substances
NO882037L (no) *	1987-06-22	1988-12-23	Marga Para La Investigacion Sa	Famotidin, polymerte former og fremstilling derav.
US5731442A (en) *	1997-03-11	1998-03-24	Albemarle Corporation	Synthesis of thiazole derivatives
US5856500A (en) *	1997-03-11	1999-01-05	Albemarle Corporation	Synthesis of thiazole derivatives
US6552047B2 (en) *	1998-11-17	2003-04-22	Nitromed, Inc.	H2 receptor antagonist compounds in combination with nitric oxide donors, compositions and methods of use
US20110143340A1 (en) *	2007-11-01	2011-06-16	Biocept, Inc.	Non-invasive isolation of fetal nucleic acid

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6056143B2 (ja) *	1979-08-02	1985-12-09	山之内製薬株式会社	アミジン誘導体ならびにその製造法
US4808589A (en) *	1982-02-20	1989-02-28	Smith Kline & French Laboratories Limited	Pyrimidone derivatives
US4496737A (en)	1982-09-27	1985-01-29	Merck & Co., Inc.	Process for preparing sulfamylamidine antisecretory agents
ES526303A0 (es) *	1983-10-07	1985-04-01	Inke Sa	Procedimiento para la obtencion de (-1amino-3-(((2-((diaminometileno) amino)-4-tiazolil)metil)tio)propilideno)sulfamida
ES532239A0 (es) *	1984-05-07	1985-08-01	Inke Sa	Procedimiento para la obtencion de la 1-amino-3-2-diamino-metilen-amino-4-tiazolil-metil-tio-propiliden-sulfamida.
ES536322A0 (es) *	1984-09-27	1985-08-01	Bioiberica	Procedimiento para la obtencion del n-aminosolfenil-3-(((2-guanidin-4-tiazonil)metil)tio) propionamidina
ES8506664A1 (es) *	1984-10-17	1985-08-01	Inke Sa	Procedimiento para la obtencion de la (1-amino-3(((2-((diamino-metilen) amino)-4-tiazolil)metil)tio)propiliden)sulfamida
HU193608B (en) *	1985-09-11	1987-11-30	Richter Gedeon Vegyeszet	Process for production of new dervatives of n-sulphanol-propion-amidine
HU194845B (en) *	1985-09-11	1988-03-28	Richter Gedeon Vegyeszet	Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin
JP3751649B2 (ja) *	1994-12-01	2006-03-01	関西ペイント株式会社	自動車外板塗膜の一時保護方法

1985
- 1985-09-11 HU HU853424A patent/HU194845B/hu unknown
1986
- 1986-08-22 CA CA000516617A patent/CA1263120A/en not_active Expired
- 1986-09-03 NL NL8602225A patent/NL8602225A/nl not_active Application Discontinuation
- 1986-09-08 AR AR305176A patent/AR240319A1/es active
- 1986-09-08 KR KR1019860007508A patent/KR910000237B1/ko not_active Expired
- 1986-09-09 GR GR862308A patent/GR862308B/el unknown
- 1986-09-09 SU SU864028107A patent/SU1450743A3/ru active
- 1986-09-09 DD DD86294264A patent/DD249479A5/de unknown
- 1986-09-10 DK DK434586A patent/DK169920B1/da not_active IP Right Cessation
- 1986-09-10 PT PT83348A patent/PT83348B/pt unknown
- 1986-09-10 NO NO863616A patent/NO163010C/no not_active IP Right Cessation
- 1986-09-10 SE SE8603797A patent/SE8603797L/xx not_active Application Discontinuation
- 1986-09-10 AU AU62569/86A patent/AU587279B2/en not_active Expired
- 1986-09-10 FI FI863657A patent/FI86423C/fi not_active IP Right Cessation
- 1986-09-10 AT AT0243486A patent/AT386824B/de not_active IP Right Cessation
- 1986-09-10 GB GB8621742A patent/GB2180237B/en not_active Expired
- 1986-09-10 BE BE0/217144A patent/BE905409A/fr not_active IP Right Cessation
- 1986-09-10 JP JP61211792A patent/JPH0645609B2/ja not_active Expired - Lifetime
- 1986-09-11 CN CN86105909A patent/CN1013674B/zh not_active Expired
- 1986-09-11 ES ES8601790A patent/ES2001677A6/es not_active Expired
1987
- 1987-07-23 US US07/077,095 patent/US4835281A/en not_active Expired - Lifetime
1993
- 1993-06-14 GE GEAP1993867A patent/GEP19960471B/en unknown

Also Published As

Publication number	Publication date
BE905409A (fr)	1986-12-31
PT83348B (pt)	1988-07-29
CA1263120A (en)	1989-11-21
FI863657A7 (fi)	1987-03-12
ATA243486A (de)	1988-03-15
DK169920B1 (da)	1995-04-03
NL8602225A (nl)	1987-04-01
US4835281A (en)	1989-05-30
AU6256986A (en)	1987-03-12
FI86423C (fi)	1992-08-25
NO863616D0 (no)	1986-09-10
JPS6296481A (ja)	1987-05-02
FI863657A0 (fi)	1986-09-10
AU587279B2 (en)	1989-08-10
FI86423B (fi)	1992-05-15
HU194845B (en)	1988-03-28
ES2001677A6 (es)	1988-06-01
GR862308B (en)	1987-01-02
KR870003078A (ko)	1987-04-15
DK434586D0 (da)	1986-09-10
NO863616L (no)	1987-03-12
GB2180237B (en)	1989-09-06
NO163010C (no)	1990-03-21
GB2180237A (en)	1987-03-25
PT83348A (pt)	1986-10-01
HUT42766A (en)	1987-08-28
GEP19960471B (en)	1996-05-13
GB8621742D0 (en)	1986-10-15
CN1013674B (zh)	1991-08-28
DK434586A (da)	1987-03-12
SE8603797L (sv)	1987-03-12
AR240319A1 (es)	1990-03-30
CN86105909A (zh)	1987-05-13
KR910000237B1 (ko)	1991-01-23
JPH0645609B2 (ja)	1994-06-15
SE8603797D0 (sv)	1986-09-10
NO163010B (no)	1989-12-11
SU1450743A3 (ru)	1989-01-07
AT386824B (de)	1988-10-25

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20060910

Publication	Publication Date	Title
DE2322880C2 (de)	1982-09-23	4-(Imidazolin-2-ylamino)-2,1,3-benzothiadiazole und Verfahren zu deren Herstellung
DE1668420A1 (de)	1970-06-25	N-substituierte Perfluoralkylsulfonamide
DE2457911A1 (de)	1975-06-12	Verfahren zur herstellung von chinazolinen
DE2505297B2 (de)	1978-08-17	Verfahren zur Herstellung von in 2- und 6-Stellung des Phenylkerns substituierten 2-Phenylamino-2-imidazolin-Derivaten
DE2826452A1 (de)	1979-01-11	Verfahren zur herstellung von substituierten guanidinen
DE69603261T2 (de)	1999-12-16	Verfahren zur herstellung von 1,2-benzisothiazolonen
DE941288C (de)	1956-04-05	Verfahren zur Herstellung substituierter 2-Imino-4-thiazoline oder von Salzen derselben bzw. von substituierten 2-Aminothiazolen
DE1770658A1 (de)	1971-11-11	N-Hydroxi-benzimidazole,ihre Herstellung und Verwendung als Herbicide
DE1795344B2 (de)	1976-05-06	Verfahren zur herstellung von 3-aminoisothiazolen
DE915809C (de)	1954-07-29	Verfahren zur Herstellung von heterocyclischen Sulfonamiden
DE2523279A1 (de)	1975-12-04	Verfahren zur herstellung von 3-trichlormethyl-5-aethoxy-1,2,4-thiadiazol
DE946804C (de)	1956-08-09	Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure
DE2166270C3 (de)	1975-10-09	Nicotinoylaminoäthansulfonyl-2amino-thiazol
DE2065698C3 (de)	1979-08-30	Verfahren zur Herstellung von 2-Isopropyl-6-methyl-4(3H)-pyrimidon
DE2536951A1 (de)	1976-03-11	Triazapentadiene, verfahren zu ihrer herstellung und ihre verwendung als milbenmittel und insektizide
DE2512702C2 (de)	1982-09-23	Substituierte 1-Amino-3-phenyl-indole, deren Salze und Verfahren zu ihrer Herstellung
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