DE2560104C2 - Verfahren zur Herstellung von in 2-und 6-Stellung des Phenylkerns substituierten 1-Benzoyl-2-phenylamino-2-imidazolinderivaten - Google Patents
Verfahren zur Herstellung von in 2-und 6-Stellung des Phenylkerns substituierten 1-Benzoyl-2-phenylamino-2-imidazolinderivatenInfo
- Publication number
- DE2560104C2 DE2560104C2 DE2560104A DE2560104A DE2560104C2 DE 2560104 C2 DE2560104 C2 DE 2560104C2 DE 2560104 A DE2560104 A DE 2560104A DE 2560104 A DE2560104 A DE 2560104A DE 2560104 C2 DE2560104 C2 DE 2560104C2
- Authority
- DE
- Germany
- Prior art keywords
- benzoyl
- imidazoline
- phenylamino
- positions
- preparation
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- VBCXKADQFPKGJN-UHFFFAOYSA-N (2-anilino-4,5-dihydroimidazol-1-yl)-phenylmethanone Chemical group C=1C=CC=CC=1C(=O)N1CCNC1=NC1=CC=CC=C1 VBCXKADQFPKGJN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 description 21
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 6
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- 239000000243 solution 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
- JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical class N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 aromatic carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UZEANKMQCCWORV-UHFFFAOYSA-N CC1=CC(C(N2C(NC(C(Cl)=CC=C3)=C3Cl)=NCC2)=O)=CC=C1 Chemical compound CC1=CC(C(N2C(NC(C(Cl)=CC=C3)=C3Cl)=NCC2)=O)=CC=C1 UZEANKMQCCWORV-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- YHEMKMZUJKPOCO-UHFFFAOYSA-N [2-(2,6-dichloroanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 YHEMKMZUJKPOCO-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000001326 carotid sinus Anatomy 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 239000002552 dosage form Substances 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 238000011835 investigation Methods 0.000 description 1
- 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 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 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
- 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 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000003867 tiredness Effects 0.000 description 1
- 208000016255 tiredness Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT547474A AT333749B (de) | 1974-07-03 | 1974-07-03 | Verfahren zur herstellung von neuen 2-arylamino-2-imidazolinderivaten |
| JP60076A JPS5283661A (en) | 1974-07-03 | 1976-01-01 | Novel 22arylaminoo22 imidazoline derivatives and salts thereof* |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2560104B2 DE2560104B2 (de) | 1981-07-16 |
| DE2560104C2 true DE2560104C2 (de) | 1982-03-25 |
Family
ID=25602211
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2560104A Expired DE2560104C2 (de) | 1974-07-03 | 1975-05-15 | Verfahren zur Herstellung von in 2-und 6-Stellung des Phenylkerns substituierten 1-Benzoyl-2-phenylamino-2-imidazolinderivaten |
| DE2521709A Expired DE2521709C3 (de) | 1974-07-03 | 1975-05-15 | Verfahren zur Herstellung von in 2- und 6- Stellung substituierten 1- Benzoyl-2-phenyl-amino-2-imidazolinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2521709A Expired DE2521709C3 (de) | 1974-07-03 | 1975-05-15 | Verfahren zur Herstellung von in 2- und 6- Stellung substituierten 1- Benzoyl-2-phenyl-amino-2-imidazolinderivaten |
Country Status (10)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5297383A (en) * | 1976-02-13 | 1977-08-16 | Ngk Spark Plug Co | Ceramic honeycomb structures for exhaust gas purification |
| JPS5499090A (en) * | 1978-01-23 | 1979-08-04 | Nissan Motor Co Ltd | Monolithic catalyst structure and production thereof |
| DE2811847A1 (de) | 1978-03-17 | 1979-09-20 | Lentia Gmbh | Neue arylaminoimidazolinderivate, deren herstellung und verwendung als arzneimittel |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPS6091220U (ja) * | 1983-11-30 | 1985-06-22 | 株式会社 土屋製作所 | ハニカム濾過エレメント |
| EP1333028A1 (en) * | 2002-01-31 | 2003-08-06 | Boehringer Ingelheim Pharma GmbH & Co.KG | 2'-Halo-3',5'-dialkoxyphen-1'-yl-imino-2-imidazolidine derivatives and the use thereof for the treatment of urinary incontinence |
| US6703409B2 (en) | 2002-01-31 | 2004-03-09 | Boehringer Ingelheim Pharma Gmbh & Co Kg | 2′-Halo-3′,5′-dialkoxyphen-1′-yl-imino-2-imidazolidine and the use thereof as a drug |
| WO2012007426A1 (en) | 2010-07-13 | 2012-01-19 | Basf Se | Azoline substituted isoxazoline benzamide compounds for combating animal pests |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741947A (en) * | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline |
-
1974
- 1974-07-03 AT AT547474A patent/AT333749B/de not_active IP Right Cessation
-
1975
- 1975-05-15 DE DE2560104A patent/DE2560104C2/de not_active Expired
- 1975-05-15 DE DE2521709A patent/DE2521709C3/de not_active Expired
- 1975-06-06 DK DK254275A patent/DK145696C/da not_active IP Right Cessation
- 1975-06-09 BG BG030228A patent/BG26527A3/xx unknown
- 1975-06-10 FI FI751721A patent/FI64145C/fi not_active IP Right Cessation
- 1975-06-19 CH CH801875A patent/CH613193A5/xx not_active IP Right Cessation
- 1975-06-23 NL NLAANVRAGE7507456,A patent/NL177402C/xx not_active IP Right Cessation
- 1975-06-24 JP JP50077063A patent/JPS5134156A/ja active Granted
- 1975-07-01 DD DD187007A patent/DD118639A1/xx unknown
- 1975-07-03 CS CS754745A patent/CS193517B2/cs unknown
-
1976
- 1976-01-01 JP JP60076A patent/JPS5283661A/ja active Pending
-
1985
- 1985-04-15 NL NL8501099A patent/NL8501099A/nl not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741947A (en) * | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline |
Also Published As
| Publication number | Publication date |
|---|---|
| FI751721A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-01-04 |
| ATA547474A (de) | 1976-03-15 |
| JPS5283661A (en) | 1977-07-12 |
| JPS5134156A (en) | 1976-03-23 |
| DK145696C (da) | 1983-07-18 |
| DK254275A (da) | 1976-01-04 |
| DE2521709C3 (de) | 1982-04-29 |
| FI64145C (fi) | 1983-10-10 |
| DD118639A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-12 |
| JPS5230516B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-09 |
| DE2521709B2 (de) | 1981-06-19 |
| DK145696B (da) | 1983-01-31 |
| NL7507456A (nl) | 1976-01-06 |
| NL177402C (nl) | 1985-09-16 |
| NL8501099A (nl) | 1985-08-01 |
| BG26527A3 (bg) | 1979-04-12 |
| DE2521709A1 (de) | 1976-02-05 |
| AT333749B (de) | 1976-12-10 |
| DE2560104B2 (de) | 1981-07-16 |
| CH613193A5 (en) | 1979-09-14 |
| CS193517B2 (en) | 1979-10-31 |
| FI64145B (fi) | 1983-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| BI | Miscellaneous see part 2 | ||
| OD | Request for examination | ||
| AC | Divided out of |
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| 8339 | Ceased/non-payment of the annual fee |