NO830388L - Fremgangsmaate for fremstilling av imidazolidinderivater - Google Patents

Fremgangsmaate for fremstilling av imidazolidinderivater

Info

Publication number: NO830388L
Authority: NO; Norway
Prior art keywords: imidazolidine; reacted; amino; alkyl; hydroxy
Prior art date: 1982-02-05

Application number

NO830388A

Other languages

English (en)

Norwegian (no)

Inventor

Thomas Purcell

Original Assignee

Synthelabo

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.)

1982-02-05

Filing date

1983-02-04

Publication date

1983-08-08

1983-02-04 Application filed by Synthelabo filed Critical Synthelabo

1983-08-08 Publication of NO830388L publication Critical patent/NO830388L/no

Links

238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
MTIMDGQILFWMJI-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazole Chemical compound CSC1=NCCN1 MTIMDGQILFWMJI-UHFFFAOYSA-N 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
229910017604 nitric acid Inorganic materials 0.000 claims description 4
RVZHUQPIBHMAEX-UHFFFAOYSA-N sodium;isocyanate Chemical compound [Na+].[N-]=C=O RVZHUQPIBHMAEX-UHFFFAOYSA-N 0.000 claims description 4
PKQWOSBJXULYBJ-UHFFFAOYSA-N 2-amino-4-(4,5-dihydro-1h-imidazol-2-ylamino)phenol Chemical compound C1=C(O)C(N)=CC(N=C2NCCN2)=C1 PKQWOSBJXULYBJ-UHFFFAOYSA-N 0.000 claims description 3
CPZPACPRIFPYFU-UHFFFAOYSA-N 2-amino-5-(4,5-dihydro-1h-imidazol-2-ylamino)phenol Chemical compound C1=C(O)C(N)=CC=C1N=C1NCCN1 CPZPACPRIFPYFU-UHFFFAOYSA-N 0.000 claims description 3
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 3
STLPJYGZOIEDAJ-UHFFFAOYSA-N 6-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=C2NC(=O)OC2=C1 STLPJYGZOIEDAJ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
LJJWDQAGYCITPB-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-ylamino)-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1N=C1NCCN1 LJJWDQAGYCITPB-UHFFFAOYSA-N 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
-1 (3-amino-4-hydroxyphenyl)-iminoimidazolidine Chemical compound 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
238000004448 titration Methods 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
JDKZJKILPQHIOY-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-ylamino)phenol Chemical compound C1=CC(O)=CC=C1N=C1NCCN1 JDKZJKILPQHIOY-UHFFFAOYSA-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
241001465754 Metazoa Species 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YTGPGCNTDJJAIP-UHFFFAOYSA-N [5-(4,5-dihydro-1h-imidazol-2-ylamino)-2-hydroxyphenyl]urea Chemical compound C1=C(O)C(NC(=O)N)=CC(N=C2NCCN2)=C1 YTGPGCNTDJJAIP-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
210000003736 gastrointestinal content Anatomy 0.000 description 2
UZSQOADVOWTDAJ-UHFFFAOYSA-N n-[4-(4,5-dihydro-1h-imidazol-2-ylamino)-2-hydroxyphenyl]formamide Chemical compound C1=C(NC=O)C(O)=CC(N=C2NCCN2)=C1 UZSQOADVOWTDAJ-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
210000001187 pylorus Anatomy 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
208000001089 Multiple system atrophy Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010031127 Orthostatic hypotension Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
UTSOXZIZVGUTCF-UHFFFAOYSA-N hydrate;hydroiodide Chemical compound O.I UTSOXZIZVGUTCF-UHFFFAOYSA-N 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002350 laparotomy Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
XLMVUJYMSWPLMK-UHFFFAOYSA-N n-[5-(4,5-dihydro-1h-imidazol-2-ylamino)-2-hydroxyphenyl]formamide Chemical compound C1=C(NC=O)C(O)=CC=C1N=C1NCCN1 XLMVUJYMSWPLMK-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Ophthalmology & Optometry (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Fats And Perfumes (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)
Emergency Protection Circuit Devices (AREA)
Control Of Transmission Device (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

NO830388A 1982-02-05 1983-02-04 Fremgangsmaate for fremstilling av imidazolidinderivater NO830388L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8201877A FR2521140A1 (fr)	1982-02-05	1982-02-05	Derives d'imidazolidine, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NO830388L true NO830388L (no)	1983-08-08

Family

ID=9270708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO830388A NO830388L (no)	1982-02-05	1983-02-04	Fremgangsmaate for fremstilling av imidazolidinderivater

Country Status (19)

Country	Link
US (1)	US4492709A (de)
EP (1)	EP0086126B1 (de)
JP (1)	JPS58146569A (de)
AT (1)	ATE14424T1 (de)
AU (1)	AU553893B2 (de)
CA (1)	CA1190933A (de)
DE (1)	DE3360411D1 (de)
DK (1)	DK47683A (de)
ES (1)	ES8403461A1 (de)
FI (1)	FI830397L (de)
FR (1)	FR2521140A1 (de)
GR (1)	GR77414B (de)
HU (1)	HU191284B (de)
IE (1)	IE830225L (de)
IL (1)	IL67835A0 (de)
NO (1)	NO830388L (de)
NZ (1)	NZ203185A (de)
PT (1)	PT76196B (de)
ZA (1)	ZA83763B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS63113077A (ja) *	1986-06-13	1988-05-18	Konica Corp	分光吸収特性等に優れたジフエニルイミダゾ−ル系染料
US5629345A (en) *	1993-07-23	1997-05-13	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
US5965620A (en) *	1993-07-23	1999-10-12	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
JPH09506622A (ja) *	1993-12-17	1997-06-30	ザ、プロクター、エンド、ギャンブル、カンパニー	α−２−アドレノセプター作動剤として有用な６−（２−イミダゾリニルアミノ）キノキサリン化合物
DE19514579A1 (de)	1995-04-20	1996-10-24	Boehringer Ingelheim Kg	Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz
WO1998023612A1 (en) *	1996-11-25	1998-06-04	The Procter & Gamble Company	2-imidazolinylaminobenzothiazole compounds useful as alpha-2 adrenoceptor agonists
WO1998023611A1 (en) *	1996-11-25	1998-06-04	The Procter & Gamble Company	2-imidazolinylaminobenzoxazole compounds useful as alpha-2 adrenoceptor agonists
SG72827A1 (en) *	1997-06-23	2000-05-23	Hoffmann La Roche	Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives
FR2805159B1 (fr)	2000-02-23	2005-06-10	Oreal	Compositions pour la teinture d'oxydation des fibres keratiniques comprenant un n-(2-hydroxybenzene)-carbamate ou un n-(2-hydroxybenzene)-uree a titre de coupleur, et procedes de teinture
WO2001094299A1 (fr) *	2000-06-08	2001-12-13	Shizuoka Coffein Co., Ltd.	Derives de benzene

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3818094A (en) *	1969-08-28	1974-06-18	Boehringer Sohn Ingelheim	Hypotensive pharmaceutical compositions containing certain 2-anilino-1,3-diazacyclopentenes-(2)
JPS5395969A (en) *	1976-12-20	1978-08-22	Wellcome Found	Imidazoline derivative and insecticide containing same
DE2806775A1 (de) *	1978-02-17	1979-08-30	Boehringer Sohn Ingelheim	Neue substituierte 2-phenylimino- imidazolidine deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
US4262005A (en) *	1978-05-31	1981-04-14	The Boots Company Limited	Compounds, compositions and methods for controlling pests
US4290971A (en) *	1979-01-19	1981-09-22	Dso "Pharmachim"	Method of preparing 2-(phenylamino)-imidazolines-(2)
ZA801680B (en) *	1979-04-03	1981-03-25	Fujisawa Pharmaceutical Co	2-imidazoline derivatives,process for the preparation thereof and the pharmaceutical composition of the same

1982
- 1982-02-05 FR FR8201877A patent/FR2521140A1/fr active Granted
1983
- 1983-01-19 DE DE8383400128T patent/DE3360411D1/de not_active Expired
- 1983-01-19 AT AT83400128T patent/ATE14424T1/de not_active IP Right Cessation
- 1983-01-19 EP EP83400128A patent/EP0086126B1/de not_active Expired
- 1983-01-25 US US06/460,993 patent/US4492709A/en not_active Expired - Fee Related
- 1983-02-04 ZA ZA83763A patent/ZA83763B/xx unknown
- 1983-02-04 PT PT76196A patent/PT76196B/pt unknown
- 1983-02-04 GR GR70417A patent/GR77414B/el unknown
- 1983-02-04 ES ES519532A patent/ES8403461A1/es not_active Expired
- 1983-02-04 DK DK47683A patent/DK47683A/da not_active Application Discontinuation
- 1983-02-04 FI FI830397A patent/FI830397L/fi not_active Application Discontinuation
- 1983-02-04 NO NO830388A patent/NO830388L/no unknown
- 1983-02-04 HU HU83395A patent/HU191284B/hu unknown
- 1983-02-04 CA CA000420966A patent/CA1190933A/en not_active Expired
- 1983-02-04 NZ NZ203185A patent/NZ203185A/xx unknown
- 1983-02-04 IE IE830225A patent/IE830225L/xx unknown
- 1983-02-04 JP JP58018018A patent/JPS58146569A/ja active Pending
- 1983-02-04 AU AU11150/83A patent/AU553893B2/en not_active Ceased
- 1983-02-04 IL IL67835A patent/IL67835A0/xx unknown

Also Published As

Publication number	Publication date
IE830225L (en)	1983-08-05
PT76196A (fr)	1983-03-01
JPS58146569A (ja)	1983-09-01
GR77414B (de)	1984-09-13
HU191284B (en)	1987-02-27
DK47683D0 (da)	1983-02-04
FR2521140B1 (de)	1984-03-16
AU553893B2 (en)	1986-07-31
FI830397A0 (fi)	1983-02-04
CA1190933A (en)	1985-07-23
FR2521140A1 (fr)	1983-08-12
DK47683A (da)	1983-08-06
DE3360411D1 (en)	1985-08-29
ATE14424T1 (de)	1985-08-15
IL67835A0 (en)	1983-06-15
ZA83763B (en)	1983-10-26
EP0086126A1 (de)	1983-08-17
AU1115083A (en)	1983-08-11
ES519532A0 (es)	1984-03-16
NZ203185A (en)	1985-07-31
PT76196B (fr)	1986-01-27
EP0086126B1 (de)	1985-07-24
ES8403461A1 (es)	1984-03-16
FI830397L (fi)	1983-08-06
US4492709A (en)	1985-01-08

Publication	Publication Date	Title
SU1375127A3 (ru)	1988-02-15	Способ получени производных 1,2-диаминоциклобутен-3,4-диона или их хлоргидратов
SU1110381A3 (ru)	1984-08-23	Способ получени производных имидазолилфениламидина
NO830388L (no)	1983-08-08	Fremgangsmaate for fremstilling av imidazolidinderivater
NO791710L (no)	1979-11-27	Analogifremgangsmaate for fremstilling av fysiologisk aktive tiadiazolderivater
WO1999062892A1 (en)	1999-12-09	Aminoazole compounds
DE3884007T2 (de)	1994-01-20	Arylpiperazinylalkylenphenylheterocyclische Verbindungen.
CA1103245A (en)	1981-06-16	Process for the manufacture of novel oxadiazolopyrimidine derivatives
IE54327B1 (en)	1989-08-30	Ergoline derivatives
AU596869B2 (en)	1990-05-17	2-(thio-linked)-pyridine-5-(4,5-dihydro-2-oxazolyl)-(thieno( 2,3-d)-imidazoles and -benzimidazoles), a process for their preparation, and their use
US4497810A (en)	1985-02-05	Thiatriazine dioxides as gastric anti-secretory agents
NO861802L (no)	1986-11-10	Nye derivater av tieno(2,3-d)imidazoler og fremgangsmaate til deres fremstilling.
US5037830A (en)	1991-08-06	Novel thiouracyl derivatives, pharmaceutical compositions containing them and process for preparing same
SU1362402A3 (ru)	1987-12-23	Способ получени производных имидазола или их солей с кислотами
JPS6323191B2 (de)	1988-05-16
SU1322979A3 (ru)	1987-07-07	Способ получени производных имидазолилфениламидина или их кислотно-аддитивных солей
US4937252A (en)	1990-06-26	2-thiazolidinone derivatives, pharmaceutical compositions containing them and process for preparing same
NO831343L (no)	1983-10-17	Furanderivater og fremgangsmaate til deres fremstilling
NO883263L (no)	1989-01-24	Fremgangsmaate for fremstilling av terapeutisk aktive benzimidazol-derivater.
NO162017B (no)	1989-07-17	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-aryl-alfa-pyridylalkansyrederivater.
NO127447B (de)	1973-06-25
PL134315B1 (en)	1985-08-31	Process for preparing novel 3'-substituted-5'-/2-amino-4-pyridyl/-1',2',4'-triazoles
DK169255B1 (da)	1994-09-26	Analogifremgangsmåde til fremstilling af thieno-isothiazol-1,1-dioxid-derivater og farmaceutisk acceptable salte heraf
US4267178A (en)	1981-05-12	Disubstituted piperazines
JPH0525140A (ja)	1993-02-02	ベンズイミダゾール誘導体
EP0008150B1 (de)	1982-04-28	2,6-Dichlorphenyl-substituierte Amino-imidazol-Derivate, Verfahren zur Herstellung dieser Derivate und diese Derivate enthaltende pharmazeutische Zusammensetzungen