CA1044240A - Synthese de derives d'arylamino-2 imidazoline-2 - Google Patents

Synthese de derives d'arylamino-2 imidazoline-2

Info

Publication number: CA1044240A
Authority: CA; Canada
Prior art keywords: formula; compound; process according; iii; imidazoline
Prior art date: 1974-01-04
Legal status (The legal status 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 status listed.): Expired

Application number

CA230,010A

Other languages

English (en)

Other versions

CA230010S (en

Inventor

Rudolf Franzmair

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Patheon Austria GmbH and Co KG

Original Assignee

Chemie Linz 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.)

1974-01-04

Filing date

1975-06-24

Publication date

1978-12-12

1974-01-04 Priority claimed from AT5474A external-priority patent/AT347117B/de

1975-06-24 Application filed by Chemie Linz AG filed Critical Chemie Linz AG

1978-12-12 Application granted granted Critical

1978-12-12 Publication of CA1044240A publication Critical patent/CA1044240A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 17
150000001875 compounds Chemical class 0.000 claims abstract description 34
150000001408 amides Chemical class 0.000 claims abstract description 18
-1 aromatic carboxylic acids Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims description 14
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
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 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000001841 imino group Chemical group [H]N=* 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
150000002462 imidazolines Chemical class 0.000 abstract description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
239000000047 product Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical class C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 7
230000001624 sedative effect Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
230000001077 hypotensive effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000005711 Benzoic acid Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical group [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
150000007513 acids Chemical class 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 2
ANGJIXOAVLXWTA-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(3-methylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC(N2C(=NCC2)NC=2C(=CC=CC=2Cl)Cl)=C1 ANGJIXOAVLXWTA-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
230000011514 reflex Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
QHNDFWPCDITBSG-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-imidazole Chemical compound C1=CC(C)=CC=C1C1=NC=CN1 QHNDFWPCDITBSG-UHFFFAOYSA-N 0.000 description 1
YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
YLMXBNACRIGGFX-UHFFFAOYSA-N C=1[C-]=NNN=1 Chemical class C=1[C-]=NNN=1 YLMXBNACRIGGFX-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
241001024304 Mino Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GYMWSBVKAPVTPI-UHFFFAOYSA-N N1N=[C-]N=C1 Chemical class N1N=[C-]N=C1 GYMWSBVKAPVTPI-UHFFFAOYSA-N 0.000 description 1
XMPHXRWCMXBQCG-UHFFFAOYSA-N N1[C-]=CC=C1.C(C)(=O)O Chemical class N1[C-]=CC=C1.C(C)(=O)O XMPHXRWCMXBQCG-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
UKIBUEVBTOXARC-UHFFFAOYSA-N [2-(2,6-dibromoanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound BrC1=CC=CC(Br)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 UKIBUEVBTOXARC-UHFFFAOYSA-N 0.000 description 1
GYJDNTLCTPWPIK-UHFFFAOYSA-N [N].N1C=NCC1 Chemical compound [N].N1C=NCC1 GYJDNTLCTPWPIK-UHFFFAOYSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 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
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
WVBFELDKHPOQCL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(4-methylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound C1=CC(C)=CC=C1N1C(NC=2C(=CC=CC=2Cl)Cl)=NCC1 WVBFELDKHPOQCL-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA230,010A 1974-01-04 1975-06-24 Synthese de derives d'arylamino-2 imidazoline-2 Expired CA1044240A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT5474A AT347117B (de)	1973-01-05	1974-01-04	Vorrichtung zum entgraten der haelse von hohlkoerpern aus kunststoff

Publications (1)

Publication Number	Publication Date
CA1044240A true CA1044240A (fr)	1978-12-12

Family

ID=3480305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA230,010A Expired CA1044240A (fr)	1974-01-04	1975-06-24	Synthese de derives d'arylamino-2 imidazoline-2

Country Status (2)

Country	Link
CA (1)	CA1044240A (fr)
SE (1)	SE417605B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4581460A (en) *	1982-01-07	1986-04-08	Chemie Linz Aktiengesellschaft	Substituted 1-benzoyl-2-phenyliminoimidazolidine derivatives

1975
- 1975-06-24 SE SE7507237A patent/SE417605B/xx not_active IP Right Cessation
- 1975-06-24 CA CA230,010A patent/CA1044240A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4581460A (en) *	1982-01-07	1986-04-08	Chemie Linz Aktiengesellschaft	Substituted 1-benzoyl-2-phenyliminoimidazolidine derivatives

Also Published As

Publication number	Publication date
SE7507237L (sv)	1976-01-05
SE417605B (sv)	1981-03-30

Publication	Publication Date	Title
EP0260817A1 (fr)	1988-03-23	Quinazolinediones et pyridopyrimidinediones
US4284768A (en)	1981-08-18	1,2-Dihydro-4-amino-2-oxo-3-quinoline-carboxylic acid derivatives
US3988345A (en)	1976-10-26	Imidazoline derivatives and the preparation thereof
US4032559A (en)	1977-06-28	N,2-dicyanoacetimidates
US4061647A (en)	1977-12-06	Thiazolidine derivatives
US3551419A (en)	1970-12-29	Amino acid amides and process for their production
KR20010024258A (ko)	2001-03-26	포스포리파제 저해제로 사용되는9,10-디히드로-9,10-에타노안트라센 유도체
GB1568398A (en)	1980-05-29	Triazolo pyridazine derivatives
CA1107740A (fr)	1981-08-25	Methode de preparation de derives de la thiazolidine- 2,4-dione
CA1044240A (fr)	1978-12-12	Synthese de derives d'arylamino-2 imidazoline-2
FI64145B (fi)	1983-06-30	Foerfarande foer framstaellning av 2-arylamino-2-imidazolinderivat
IL116384A (en)	1996-10-16	Ylidene compounds and their preparation
US3654275A (en)	1972-04-04	Quinoxalinecarboxamide antiinflammatory agents
US3336326A (en)	1967-08-15	Novel imidazole carboxamides
US4142051A (en)	1979-02-27	Arylaminoimidazoline derivatives
US4200759A (en)	1980-04-29	Preparation of imidazo[2,1-a]isoindole compounds
US5059599A (en)	1991-10-22	Derivatives of 1-phenyl 1,4-dihydro 3-amino 4-oxo pyridazines, their preparation and their use in therapy
US4221798A (en)	1980-09-09	Hypotensive 2-heterocycloamino-imidazolines
US3328404A (en)	1967-06-27	Derivatives of pyrazine
US3426017A (en)	1969-02-04	Sulfonylurea compounds
US3536725A (en)	1970-10-27	Cyanoethylated derivatives of 2,3,4,6,7,12-hexahydroindolo(2,3-alpha)-quinolizine
US4581460A (en)	1986-04-08	Substituted 1-benzoyl-2-phenyliminoimidazolidine derivatives
US3417080A (en)	1968-12-17	Sulfamylanthranilic acid amides and process for preparing them
US3433802A (en)	1969-03-18	3-(n-lower-alkylanilino)pyrrolidines
US4118501A (en)	1978-10-03	Thiazolidine derivatives

CA1044240A - Synthese de derives d'arylamino-2 imidazoline-2 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=3480305

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

Also Published As

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