CH495360A - Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen - Google Patents

Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen

Info

Publication number: CH495360A
Authority: CH; Switzerland
Prior art keywords: alkyl; phenylenediamine; water; carbalkoxyaminobenzimidazoles; soln
Prior art date: 1967-03-22

Application number

CH406168A

Other languages

German (de)

English (en)

Inventor

John Stedman Robert

Original Assignee

Smith Kline French Lab

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.)

1967-03-22

Filing date

1968-03-19

Publication date

1970-08-31

1968-03-19 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1970-08-31 Publication of CH495360A publication Critical patent/CH495360A/de

Links

125000000217 alkyl group Chemical group 0.000 title claims abstract description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 15
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 title abstract description 5
125000005055 alkyl alkoxy group Chemical group 0.000 title abstract 2
230000000507 anthelmentic effect Effects 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 15
WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 claims abstract description 7
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000009833 condensation Methods 0.000 claims description 9
230000005494 condensation Effects 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
239000003929 acidic solution Substances 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 18
238000010992 reflux Methods 0.000 abstract description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
-1 alkyl chloroformate Chemical compound 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
235000011150 stannous chloride Nutrition 0.000 description 5
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
UNNSZBMRSVTMLC-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.CCCCC1=CC=C(N)C(N)=C1 UNNSZBMRSVTMLC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001494479 Pecora Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
SXQBFCVVZIYXHV-UHFFFAOYSA-N 1-nitro-4-propylbenzene Chemical compound CCCC1=CC=C([N+]([O-])=O)C=C1 SXQBFCVVZIYXHV-UHFFFAOYSA-N 0.000 description 1
VUMCVANUWQZNGD-UHFFFAOYSA-N 2-nitro-4-propoxyaniline Chemical compound CCCOC1=CC=C(N)C([N+]([O-])=O)=C1 VUMCVANUWQZNGD-UHFFFAOYSA-N 0.000 description 1
UACSJWZBISFLIW-UHFFFAOYSA-N 2-nitro-4-propylaniline Chemical compound CCCC1=CC=C(N)C([N+]([O-])=O)=C1 UACSJWZBISFLIW-UHFFFAOYSA-N 0.000 description 1
OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
UUAOMJOZLSTWIP-UHFFFAOYSA-N 4-propoxybenzene-1,2-diamine Chemical compound CCCOC1=CC=C(N)C(N)=C1 UUAOMJOZLSTWIP-UHFFFAOYSA-N 0.000 description 1
OAPDPORYXWQVJE-UHFFFAOYSA-N 4-propylaniline Chemical compound CCCC1=CC=C(N)C=C1 OAPDPORYXWQVJE-UHFFFAOYSA-N 0.000 description 1
ZPZZLBVKKPQYAK-UHFFFAOYSA-N 4-propylbenzene-1,2-diamine Chemical compound CCCC1=CC=C(N)C(N)=C1 ZPZZLBVKKPQYAK-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000243974 Haemonchus contortus Species 0.000 description 1
241000243780 Heligmosomoides polygyrus Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241001137882 Nematodirus Species 0.000 description 1
241000510960 Oesophagostomum Species 0.000 description 1
241000283898 Ovis Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000975692 Syphacia obvelata Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000008061 acetanilides Chemical class 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 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
239000006227 byproduct Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
GUPWNYUKYICHQX-UHFFFAOYSA-N carbonobromidic acid Chemical compound OC(Br)=O GUPWNYUKYICHQX-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
UQRJGKNAIMJVTJ-UHFFFAOYSA-N ethyl N-(ethoxycarbonylcarbamothioyl)carbamate Chemical compound C(=S)(NC(=O)OCC)NC(=O)OCC UQRJGKNAIMJVTJ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
JBTCHCWUNMZNEO-UHFFFAOYSA-N n-phenylhexanamide Chemical compound CCCCCC(=O)NC1=CC=CC=C1 JBTCHCWUNMZNEO-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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

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)

CH406168A 1967-03-22 1968-03-19 Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen CH495360A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62500967A	1967-03-22	1967-03-22
US64269467A	1967-06-01	1967-06-01

Publications (1)

Publication Number	Publication Date
CH495360A true CH495360A (de)	1970-08-31

Family

ID=27089805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH406168A CH495360A (de)	1967-03-22	1968-03-19	Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen

Country Status (6)

Country	Link
CH (1)	CH495360A (fr)
DE (1)	DE1770010C3 (fr)
DK (1)	DK131821C (fr)
FR (1)	FR1556824A (fr)
IT (1)	IT1043780B (fr)
SE (1)	SE348197B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1116425B (de) *	1958-10-02	1961-11-02	Electroacustic Gmbh	Phonogeraet
DE1163044B (de) *	1961-05-23	1964-02-13	Electroacustic Gmbh	Phonokoffer
BE793358A (fr) *	1971-12-27	1973-06-27	Hoechst Ag	Nouveaux derives de 2-carbalcoxy-amino-benzimidazole presentantune activite anthelmintique et leur procede de preparation
DE2227919C2 (de) *	1972-06-08	1982-12-23	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Benzimidazol-2-yl-carbaminsäure-methylester
IT1076022B (it) *	1977-04-20	1985-04-22	Montedison Spa	Benzimidazolcarbammati antielmintici

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE666795A (fr) *	1964-08-04	1966-01-13

1968
- 1968-03-04 DK DK88668A patent/DK131821C/da not_active IP Right Cessation
- 1968-03-18 IT IT1376868A patent/IT1043780B/it active
- 1968-03-19 CH CH406168A patent/CH495360A/de not_active IP Right Cessation
- 1968-03-20 DE DE19681770010 patent/DE1770010C3/de not_active Expired
- 1968-03-20 SE SE370368A patent/SE348197B/xx unknown
- 1968-03-20 FR FR1556824D patent/FR1556824A/fr not_active Expired

Also Published As

Publication number	Publication date
DE1770010B2 (de)	1981-07-23
DE1770010A1 (de)	1971-09-16
DK131821B (da)	1975-09-08
FR1556824A (fr)	1969-02-07
SE348197B (fr)	1972-08-28
DK131821C (da)	1976-03-08
DE1770010C3 (de)	1982-05-06
IT1043780B (it)	1980-02-29

Legal Events

Date	Code	Title	Description
1982-11-15	PFA	Name/firm changed	Owner name: SMITHKLINE CORPORATION DANN IN SMITHKLINE BECKMA
1988-05-31	PL	Patent ceased

Publication	Publication Date	Title
DE2165554A1 (de)	1973-07-05	Verfahren zur herstellung von 1,2,4triazin-5-on-derivaten
CH495360A (de)	1970-08-31	Verfahren zur Herstellung von 2-Carbalkoxyamino-benzimidazolen
DE2632402A1 (de)	1977-02-10	Verfahren zur herstellung von heterocyclischer verbindungen
DE959191C (de)	1957-02-28	Verfahren zur Herstellung von 5-Amino-1, 2, 4-thiodiazolen
EP0179408A2 (fr)	1986-04-30	Amidoalkylmélamines et aminoalkylmélamines et procédé pour leur préparation
CH610330A5 (en)	1979-04-12	Process for the preparation of novel ergopeptins
CH507277A (de)	1971-05-15	Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine
CH498135A (de)	1970-10-31	Verfahren zur Herstellung von neuen Furazanderivaten
DE2640616C3 (de)	1980-11-27	Verfahren zur Herstellung von N-Acyl-2-aiylglycinen
DE2128905A1 (de)	1973-01-04	Verfahren zur aminoalkylierung tertiaerer amine
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
DE1235929B (de)	1967-03-09	Verfahren zur Herstellung von 2-(2'-Pyrazinyl)-benzimidazol und seinen Salzen
AT287710B (de)	1971-02-10	Verfahren zur Herstellung von substituierten 3-Amino-sydnoniminen und deren Salzen
AT209897B (de)	1960-06-25	Verfahren zur Herstellung von neuen O- bzw. N-2,3,4,6-Tetrajodbenzoylverbindungen
AT229874B (de)	1963-10-25	Verfahren zur Herstellung von neuen (5- oder 6)-Alkyl- und 5, 6-Dialkyl-3-alkoxy-pyrazinen
DE925470C (de)	1955-03-21	Verfahren zur Herstellung von Additionsprodukten aus Carbonylverbindungen, Aminen und Schwefeldioxyd
CH507255A (de)	1971-05-15	Verfahren zur Herstellung von 2-(Halogenphenylamino)-imidazolin-2-Derivaten
DE2742158B2 (de)	1979-08-02	Verfahren zur Herstellung substituierter Harnstoffe
AT244344B (de)	1965-12-27	Verfahren zur Herstellung von neuen Pyrimidinverbindungen
AT366029B (de)	1982-03-10	Verfahren zur herstellung von neuen o-nitrophenyl-thioallophansaeurealkylestern
AT269864B (de)	1969-04-10	Verfahren zur Herstellung von neuen Pyrrylaminoketonderivaten und ihren Salzen
DE1770874B2 (de)	1977-09-15	Verfahren zur herstellung von 2-(2,6- dichlorphenylamino)-imidazolin-2
AT73644B (de)	1917-08-10	Verfahren zur Darstellung der Ester tertiärer Alkohole.
AT347419B (de)	1978-12-27	Verfahren zur herstellung von beta,beta'- thiodipropionsaeurediamid
CH519515A (de)	1972-02-29	Verfahren zur Herstellung von 2-(4'-Thiazolyl)-benzimidazol