IL29692A - 2-(halophenoxy methyl)-2-imidazolines - Google Patents
2-(halophenoxy methyl)-2-imidazolinesInfo
- Publication number
- IL29692A IL29692A IL2969268A IL2969268A IL29692A IL 29692 A IL29692 A IL 29692A IL 2969268 A IL2969268 A IL 2969268A IL 2969268 A IL2969268 A IL 2969268A IL 29692 A IL29692 A IL 29692A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- imidazoline
- compound
- hydrochloride
- dichlorophenoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 72
- -1 2- (substituted phenoxy-methyl)-2-imidazoline compounds Chemical class 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 24
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- AOMZMOWSWJHDRD-UHFFFAOYSA-N 2-[(3,4-dichlorophenoxy)methyl]-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1OCC1=NCCN1 AOMZMOWSWJHDRD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- XORHKBABGUOTPY-UHFFFAOYSA-N 2-[(2,6-dibromophenoxy)methyl]-4,5-dihydro-1H-imidazole Chemical compound BrC1=C(OCC=2NCCN2)C(=CC=C1)Br XORHKBABGUOTPY-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- DBJIWIIHWROFRG-UHFFFAOYSA-N Cl.BrC1=C(OCC=2NCCN2)C(=CC=C1)Br Chemical compound Cl.BrC1=C(OCC=2NCCN2)C(=CC=C1)Br DBJIWIIHWROFRG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- JYMUDVGNSULKOS-UHFFFAOYSA-N 2,6-dichloro-4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)aniline dihydrochloride Chemical compound Cl.Cl.NC1=C(C=C(OCC=2NCCN2)C=C1Cl)Cl JYMUDVGNSULKOS-UHFFFAOYSA-N 0.000 claims description 2
- SHZQDCSEIZEYLY-UHFFFAOYSA-N 4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)-2-(trifluoromethyl)aniline Chemical compound NC1=C(C=C(OCC=2NCCN2)C=C1)C(F)(F)F SHZQDCSEIZEYLY-UHFFFAOYSA-N 0.000 claims description 2
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- XVODMRNPYUMFHH-UHFFFAOYSA-N Cl.NC1=CC(=C(OCC=2NCCN2)C(=C1)Cl)Cl Chemical compound Cl.NC1=CC(=C(OCC=2NCCN2)C(=C1)Cl)Cl XVODMRNPYUMFHH-UHFFFAOYSA-N 0.000 description 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
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- JXGKMBIZNPLXNS-UHFFFAOYSA-N N-[2-chloro-4-(cyanomethoxy)phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=C(OCC#N)C=C1)Cl JXGKMBIZNPLXNS-UHFFFAOYSA-N 0.000 description 1
- FKMNGEPUVVPHKW-UHFFFAOYSA-N N-[3,5-dibromo-4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)phenyl]acetamide hydrochloride Chemical compound Cl.C(C)(=O)NC1=CC(=C(OCC=2NCCN2)C(=C1)Br)Br FKMNGEPUVVPHKW-UHFFFAOYSA-N 0.000 description 1
- XVIYAPXLYXFAOD-UHFFFAOYSA-N N-[4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)-2-(trifluoromethyl)phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=C(OCC=2NCCN2)C=C1)C(F)(F)F XVIYAPXLYXFAOD-UHFFFAOYSA-N 0.000 description 1
- HNPSPTAZRQPWLV-UHFFFAOYSA-N N-[4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)-2-(trifluoromethyl)phenyl]acetamide 4-methylbenzenesulfonic acid Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(=O)NC1=C(C=C(OCC=2NCCN2)C=C1)C(F)(F)F HNPSPTAZRQPWLV-UHFFFAOYSA-N 0.000 description 1
- LWFLWQPXMJAOBG-UHFFFAOYSA-N N-[4-(4,5-dihydro-1H-imidazol-2-ylmethoxy)-2-(trifluoromethyl)phenyl]acetamide hydrochloride Chemical compound Cl.C(C)(=O)NC1=C(C=C(OCC=2NCCN2)C=C1)C(F)(F)F LWFLWQPXMJAOBG-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
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- RJIFOLIXFDOGGT-UHFFFAOYSA-N S(=O)(=O)(O)O.ClC1=C(OCC=2NCCN2)C(=CC=C1)Cl Chemical compound S(=O)(=O)(O)O.ClC1=C(OCC=2NCCN2)C(=CC=C1)Cl RJIFOLIXFDOGGT-UHFFFAOYSA-N 0.000 description 1
- MSFIPIJPFRAHQQ-UHFFFAOYSA-N S(=O)(=O)(O)O.ClC=1C=C(OCC=2NCCN2)C=CC1Cl Chemical compound S(=O)(=O)(O)O.ClC=1C=C(OCC=2NCCN2)C=CC1Cl MSFIPIJPFRAHQQ-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- ZLNAMJBQVPHDFW-UHFFFAOYSA-N butanedioic acid 2-[(2,6-dibromophenoxy)methyl]-4,5-dihydro-1H-imidazole Chemical compound C(CCC(=O)O)(=O)O.BrC1=C(OCC=2NCCN2)C(=CC=C1)Br ZLNAMJBQVPHDFW-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000324 minimal toxicity Toxicity 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 230000005371 pilomotor reflex Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62830267A | 1967-04-04 | 1967-04-04 | |
| US62830167A | 1967-04-04 | 1967-04-04 | |
| US62830367A | 1967-04-04 | 1967-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29692A true IL29692A (en) | 1971-08-25 |
Family
ID=27417443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2969268A IL29692A (en) | 1967-04-04 | 1968-03-26 | 2-(halophenoxy methyl)-2-imidazolines |
Country Status (11)
| Country | Link |
|---|---|
| CH (1) | CH505832A (enrdf_load_stackoverflow) |
| DE (1) | DE1770104C3 (enrdf_load_stackoverflow) |
| DK (1) | DK135452B (enrdf_load_stackoverflow) |
| FI (1) | FI49613C (enrdf_load_stackoverflow) |
| FR (2) | FR1579552A (enrdf_load_stackoverflow) |
| GB (1) | GB1180862A (enrdf_load_stackoverflow) |
| IL (1) | IL29692A (enrdf_load_stackoverflow) |
| NL (1) | NL160255C (enrdf_load_stackoverflow) |
| NO (1) | NO122481B (enrdf_load_stackoverflow) |
| SE (1) | SE342626B (enrdf_load_stackoverflow) |
| YU (1) | YU33690B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3842798A1 (de) * | 1988-12-20 | 1990-06-21 | Hoechst Ag | Imidazolinderivate enthaltende mittel zur wirtstiersystemischen bekaempfung von ektoparasiten sowie neue imidazolinderivate |
-
1968
- 1968-03-22 NO NO111968A patent/NO122481B/no unknown
- 1968-03-26 IL IL2969268A patent/IL29692A/en unknown
- 1968-04-01 SE SE428068A patent/SE342626B/xx unknown
- 1968-04-01 DE DE19681770104 patent/DE1770104C3/de not_active Expired
- 1968-04-03 DK DK146768A patent/DK135452B/da not_active IP Right Cessation
- 1968-04-03 GB GB1606068A patent/GB1180862A/en not_active Expired
- 1968-04-03 NL NL6804672A patent/NL160255C/xx not_active IP Right Cessation
- 1968-04-03 FR FR1579552D patent/FR1579552A/fr not_active Expired
- 1968-04-03 CH CH488468A patent/CH505832A/de not_active IP Right Cessation
- 1968-04-03 YU YU76568A patent/YU33690B/xx unknown
- 1968-04-04 FI FI93368A patent/FI49613C/fi active
- 1968-07-03 FR FR157620A patent/FR7668M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1579552A (enrdf_load_stackoverflow) | 1969-08-29 |
| NL160255C (nl) | 1979-10-15 |
| DE1770104B2 (de) | 1978-11-23 |
| YU76568A (en) | 1977-08-31 |
| DE1770104C3 (de) | 1979-08-23 |
| FI49613B (enrdf_load_stackoverflow) | 1975-04-30 |
| DK135452C (enrdf_load_stackoverflow) | 1977-10-17 |
| FR7668M (enrdf_load_stackoverflow) | 1970-02-09 |
| CH505832A (de) | 1971-04-15 |
| FI49613C (fi) | 1975-08-11 |
| NL160255B (nl) | 1979-05-15 |
| SE342626B (enrdf_load_stackoverflow) | 1972-02-14 |
| YU33690B (en) | 1978-02-28 |
| DK135452B (da) | 1977-05-02 |
| NL6804672A (enrdf_load_stackoverflow) | 1968-10-07 |
| DE1770104A1 (de) | 1971-09-23 |
| GB1180862A (en) | 1970-02-11 |
| NO122481B (enrdf_load_stackoverflow) | 1971-07-05 |
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