NO133230B - - Google Patents
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- Publication number
- NO133230B NO133230B NO4381/71A NO438171A NO133230B NO 133230 B NO133230 B NO 133230B NO 4381/71 A NO4381/71 A NO 4381/71A NO 438171 A NO438171 A NO 438171A NO 133230 B NO133230 B NO 133230B
- Authority
- NO
- Norway
- Prior art keywords
- branched
- tetrahydronaphthalene
- straight
- imidazolin
- ylmethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000002462 imidazolines Chemical class 0.000 claims abstract 2
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- -1 benzene norbornanes Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000005526 vasoconstrictor agent Substances 0.000 description 3
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229940124572 antihypotensive agent Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ORCQJRXQASSNAQ-UHFFFAOYSA-N 1,8,9,10,11,12-hexahydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-diene Chemical compound C12=CC=CC=C2C2CCC1CC2 ORCQJRXQASSNAQ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- ILMCRZOMKCLIFZ-UHFFFAOYSA-N benzonorbornene Chemical compound C12=CC=CC=C2C2CCC1C2 ILMCRZOMKCLIFZ-UHFFFAOYSA-N 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 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
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005016 naphazoline Drugs 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 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
-
- 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
- C07D233/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3239370 | 1970-11-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133230B true NO133230B (nl) | 1975-12-22 |
| NO133230C NO133230C (nl) | 1976-03-31 |
Family
ID=11235315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4381/71A NO133230C (nl) | 1970-11-30 | 1971-11-29 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3793338A (nl) |
| JP (1) | JPS5038109B1 (nl) |
| AT (1) | AT308100B (nl) |
| AU (1) | AU456468B2 (nl) |
| BE (1) | BE775867A (nl) |
| CA (1) | CA957379A (nl) |
| CH (1) | CH570378A5 (nl) |
| DE (1) | DE2158468A1 (nl) |
| ES (1) | ES397453A1 (nl) |
| FR (1) | FR2115490B1 (nl) |
| GB (1) | GB1317514A (nl) |
| IL (1) | IL38142A (nl) |
| NL (1) | NL7116223A (nl) |
| NO (1) | NO133230C (nl) |
| SE (1) | SE377801B (nl) |
| SU (1) | SU408475A3 (nl) |
| ZA (1) | ZA717636B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1548875A (en) * | 1975-06-23 | 1979-07-18 | Mar Pha Etu Expl Marques | Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions |
| US4540705A (en) * | 1983-03-14 | 1985-09-10 | Sterling Drug Inc. | Antidepressant imidazolines and related compounds |
| JPS6036426U (ja) * | 1983-08-16 | 1985-03-13 | 筑豊金網販売株式会社 | 植生アンカ− |
| DE10063294A1 (de) * | 2000-12-19 | 2002-07-04 | Aventis Pharma Gmbh | Substituierte Heterocyclo-Norbornylamino-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1971
- 1971-11-09 GB GB5196971A patent/GB1317514A/en not_active Expired
- 1971-11-12 AU AU35640/71A patent/AU456468B2/en not_active Expired
- 1971-11-15 IL IL38142A patent/IL38142A/en unknown
- 1971-11-15 ZA ZA717636A patent/ZA717636B/xx unknown
- 1971-11-23 SU SU1715464A patent/SU408475A3/ru active
- 1971-11-25 DE DE19712158468 patent/DE2158468A1/de active Pending
- 1971-11-25 NL NL7116223A patent/NL7116223A/xx unknown
- 1971-11-26 BE BE775867A patent/BE775867A/xx unknown
- 1971-11-26 US US00202638A patent/US3793338A/en not_active Expired - Lifetime
- 1971-11-29 CA CA128,779A patent/CA957379A/en not_active Expired
- 1971-11-29 CH CH1736571A patent/CH570378A5/xx not_active IP Right Cessation
- 1971-11-29 NO NO4381/71A patent/NO133230C/no unknown
- 1971-11-29 SE SE7115226A patent/SE377801B/xx unknown
- 1971-11-29 AT AT1027571A patent/AT308100B/de not_active IP Right Cessation
- 1971-11-29 ES ES397453A patent/ES397453A1/es not_active Expired
- 1971-11-30 JP JP46096726A patent/JPS5038109B1/ja active Pending
- 1971-11-30 FR FR7142880A patent/FR2115490B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH570378A5 (nl) | 1975-12-15 |
| IL38142A (en) | 1976-05-31 |
| AT308100B (de) | 1973-06-25 |
| IL38142A0 (en) | 1972-01-27 |
| SE377801B (nl) | 1975-07-28 |
| FR2115490A1 (nl) | 1972-07-07 |
| NL7116223A (nl) | 1972-06-01 |
| ZA717636B (en) | 1973-07-25 |
| FR2115490B1 (nl) | 1974-11-15 |
| AU3564071A (en) | 1973-05-17 |
| GB1317514A (en) | 1973-05-23 |
| NO133230C (nl) | 1976-03-31 |
| US3793338A (en) | 1974-02-19 |
| ES397453A1 (es) | 1975-03-16 |
| AU456468B2 (en) | 1974-12-19 |
| BE775867A (fr) | 1972-05-26 |
| DE2158468A1 (de) | 1972-07-13 |
| JPS5038109B1 (nl) | 1975-12-06 |
| CA957379A (en) | 1974-11-05 |
| SU408475A3 (nl) | 1973-12-10 |
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