CS237317B2 - Processing of alkylthiobenzimidazole derivatives - Google Patents

Processing of alkylthiobenzimidazole derivatives Download PDF

Info

Publication number: CS237317B2
Authority: CS; Czechoslovakia
Prior art keywords: amino; benzimidazole; formula; defined above; alkoxycarbonyl
Prior art date: 1979-12-04

Application number

CS808283A

Other languages

Czech (cs)

English (en)

Inventor

Sandor Szoeke

Gyoergy Lugosi

Maria Bakonyi

Gyoergy Csermely

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1979-12-04

Filing date

1980-11-28

Publication date

1985-07-16

1980-11-28 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1984-12-14 Priority to CS849804A priority Critical patent/CS254979B2/cs

1985-07-16 Publication of CS237317B2 publication Critical patent/CS237317B2/cs

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000012320 chlorinating reagent Substances 0.000 claims description 4
150000002739 metals Chemical class 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 17
239000000047 product Substances 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
-1 alkoxycarbonyl cyanamide Chemical compound 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NMHSXXPZLXHOJO-UHFFFAOYSA-N 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2NC(NC(=O)OC)=NC2=C1 NMHSXXPZLXHOJO-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
SOMKOFZJHWCRCJ-UHFFFAOYSA-N 3h-benzimidazole-5-thiol Chemical compound SC1=CC=C2NC=NC2=C1 SOMKOFZJHWCRCJ-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
KXPVTEAMOUVXHO-UHFFFAOYSA-N methyl n-(6-sulfanyl-1h-benzimidazol-2-yl)carbamate Chemical compound SC1=CC=C2NC(NC(=O)OC)=NC2=C1 KXPVTEAMOUVXHO-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
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 description 2
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
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 1
VXLKZBRLFFGAQT-UHFFFAOYSA-N 3h-benzimidazole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2N=CNC2=C1 VXLKZBRLFFGAQT-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LLINMKPTLYWPOJ-UHFFFAOYSA-N ethyl n-(6-ethylsulfanyl-1h-benzimidazol-2-yl)carbamate Chemical compound CCSC1=CC=C2NC(NC(=O)OCC)=NC2=C1 LLINMKPTLYWPOJ-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
VCKJSKHOGHYRTC-UHFFFAOYSA-N methyl N-(4-sulfanyl-1H-benzimidazol-2-yl)carbamate Chemical compound SC1=CC=CC=2N=C(NC=21)NC(=O)OC VCKJSKHOGHYRTC-UHFFFAOYSA-N 0.000 description 1
UEGYQFTUDWBPHS-UHFFFAOYSA-N methyl n-(6-chlorosulfonyl-1h-benzimidazol-2-yl)carbamate;hydrochloride Chemical compound Cl.ClS(=O)(=O)C1=CC=C2NC(NC(=O)OC)=NC2=C1 UEGYQFTUDWBPHS-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
238000001953 recrystallisation 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
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Tropical Medicine & Parasitology (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Paper (AREA)
Lubricants (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CS808283A 1979-12-04 1980-11-28 Processing of alkylthiobenzimidazole derivatives CS237317B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS849804A CS254979B2 (cs)	1979-12-04	1984-12-14	Způsob výroby nových derivátů benzimidazolthiolu

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79CI1993A HU182782B (en)	1979-12-04	1979-12-04	Process for producing alkylthio-benzimidazoles

Publications (1)

Publication Number	Publication Date
CS237317B2 true CS237317B2 (en)	1985-07-16

Family

ID=10994778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS808283A CS237317B2 (en)	1979-12-04	1980-11-28	Processing of alkylthiobenzimidazole derivatives

Country Status (15)

Country	Link
US (1)	US4368328A (pl)
EP (1)	EP0031473B1 (pl)
JP (1)	JPS5695172A (pl)
AT (1)	ATE7692T1 (pl)
CS (1)	CS237317B2 (pl)
DD (1)	DD154976A5 (pl)
DE (1)	DE3068071D1 (pl)
DK (1)	DK160423C (pl)
FI (1)	FI74278C (pl)
GR (1)	GR72924B (pl)
HU (1)	HU182782B (pl)
IL (1)	IL61585A (pl)
PL (1)	PL128450B1 (pl)
SU (2)	SU1126208A3 (pl)
YU (1)	YU42712B (pl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU196185B (en) *	1984-12-19	1988-10-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing benzimidazol-thiol derivatives
HU200167B (en) *	1987-07-30	1990-04-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing substituted benzimidazole derivatives
DE4340915A1 (de) *	1993-02-23	1994-08-25	Heidelberger Druckmasch Ag	Auswechselbare Andrückhülse
CN1056368C (zh) *	1996-04-17	2000-09-13	常州市合成材料厂	阿苯达唑的制备工艺

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2654762A (en) *	1951-07-14	1953-10-06	Ciba Pharm Prod Inc	Iodinated substituted mercaptoimidazoles
DE2441202C2 (de) *	1974-08-28	1986-05-28	Hoechst Ag, 6230 Frankfurt	2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel
US4080461A (en) *	1975-11-03	1978-03-21	Syntex (U.S.A.) Inc.	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
SE443977B (sv) *	1977-05-10	1986-03-17	Chinoin Gyogyszer Es Vegyeszet	Forfarande for framstellning av 5(6)-tio-bensimidazolderivat

1979
- 1979-12-04 HU HU79CI1993A patent/HU182782B/hu not_active IP Right Cessation
1980
- 1980-11-28 CS CS808283A patent/CS237317B2/cs unknown
- 1980-11-28 IL IL61585A patent/IL61585A/xx not_active IP Right Cessation
- 1980-11-28 FI FI803706A patent/FI74278C/fi not_active IP Right Cessation
- 1980-12-02 EP EP80107505A patent/EP0031473B1/de not_active Expired
- 1980-12-02 DE DE8080107505T patent/DE3068071D1/de not_active Expired
- 1980-12-02 AT AT80107505T patent/ATE7692T1/de active
- 1980-12-03 US US06/212,628 patent/US4368328A/en not_active Expired - Lifetime
- 1980-12-03 YU YU3056/80A patent/YU42712B/xx unknown
- 1980-12-03 DD DD80225693A patent/DD154976A5/de not_active IP Right Cessation
- 1980-12-03 DK DK515980A patent/DK160423C/da not_active IP Right Cessation
- 1980-12-03 GR GR63541A patent/GR72924B/el unknown
- 1980-12-03 PL PL1980228234A patent/PL128450B1/pl unknown
- 1980-12-04 SU SU803212701A patent/SU1126208A3/ru active
- 1980-12-04 JP JP17030880A patent/JPS5695172A/ja active Granted
1981
- 1981-04-13 SU SU813269655A patent/SU981316A1/ru active

Also Published As

Publication number	Publication date
PL228234A1 (pl)	1981-08-21
GR72924B (pl)	1984-01-11
JPS5695172A (en)	1981-08-01
IL61585A0 (en)	1980-12-31
YU305680A (en)	1983-10-31
DK515980A (da)	1981-06-05
SU1126208A3 (ru)	1984-11-23
FI74278C (fi)	1988-01-11
DK160423B (da)	1991-03-11
DE3068071D1 (en)	1984-07-05
DD154976A5 (de)	1982-05-05
HU182782B (en)	1984-03-28
FI74278B (fi)	1987-09-30
EP0031473B1 (de)	1984-05-30
JPS6337103B2 (pl)	1988-07-22
US4368328A (en)	1983-01-11
SU981316A1 (ru)	1982-12-15
FI803706L (fi)	1981-06-05
IL61585A (en)	1986-04-29
DK160423C (da)	1991-09-16
ATE7692T1 (de)	1984-06-15
PL128450B1 (en)	1984-01-31
YU42712B (en)	1988-12-31
EP0031473A1 (de)	1981-07-08

Publication	Publication Date	Title
US3773960A (en)	1973-11-20	Acaracidal compositions and methods comprising aliphatically substituted thiosulfinyl-and sulfonyl-alkyl-2,4,5-trihalogeno imidazoles
US3564607A (en)	1971-02-16	Halogenated aryloxyacetyl cyanamides
JPS6241226B2 (pl)	1987-09-02
CS237317B2 (en)	1985-07-16	Processing of alkylthiobenzimidazole derivatives
US4487936A (en)	1984-12-11	Preparation of alkylthiobenzimidazoles
CS254979B2 (cs)	1988-02-15	Způsob výroby nových derivátů benzimidazolthiolu
EP0069445B1 (en)	1986-10-01	Process for making benzimidazoles
SU999974A3 (ru)	1983-02-23	Способ получени конденсированных производных пиримидина или их солей
DE69221698T2 (de)	1998-02-19	Verfahren zur Herstellung von Sulfonylharnstoffen
SU1183503A1 (ru)	1985-10-07	Способ получени @ -замещенных имидазолов или бензимидазолов
US3929789A (en)	1975-12-30	Pyrimidinyl acetic acid derivatives and processes for their production
EP0080555B1 (de)	1987-01-07	Verfahren zur Herstellung von 5(6)-Thiocyano-benzimidazol-Derivaten
JPH0563474B2 (pl)	1993-09-10
KR100351743B1 (ko)	2002-09-11	Ｎ,ｎ-디싸이클로헥실-2-벤조티아졸 설펜아미드의 제조방법
Griffiths et al.	1980	The chemistry of o-phenylenedi-isothiocyanate. Part 3. Studies on the syntheses of heterocyclic compounds
SU437294A1 (ru)	1974-07-25	Способ получени производных 2-амино-дигидро-бензодиазепинона
SU1409629A1 (ru)	1988-07-15	2,4,6-Трис-(4 -карбоксифенокси)-1,3,5-триазин в качестве полупродукта в синтезе отвердител эпоксидиановой смолы
JPS6327346B2 (pl)	1988-06-02
CZ298595A3 (en)	1996-04-17	Process for preparing n-cyanodithioiminocarbonates and 3-mercapto-5-amino-1h-1,2,4-triazole
CS196222B2 (cs)	1980-03-31	Způsob výroby nových oktahalogensulfoftaleinů
CS221135B1 (cs)	1983-04-29	Ethery 2,6-dimelhyl-3,5-dichlor-4-hydroxypyridinu a způsob jejich výroby
PL71736B1 (pl)	1974-06-29
NO744715L (pl)	1975-07-28
PL140422B1 (en)	1987-04-30	Process for preparing 1-/p-chlorobenzyl/-2-methylbenzimidazole
CN101163686A (zh)	2008-04-16	二羟基氯三嗪的盐的制备方法