ES449161A1 - Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions - Google Patents
Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositionsInfo
- Publication number
- ES449161A1 ES449161A1 ES449161A ES449161A ES449161A1 ES 449161 A1 ES449161 A1 ES 449161A1 ES 449161 A ES449161 A ES 449161A ES 449161 A ES449161 A ES 449161A ES 449161 A1 ES449161 A1 ES 449161A1
- Authority
- ES
- Spain
- Prior art keywords
- radical
- formula
- carbon atoms
- hydrogen
- see formula
- 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
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 title 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003254 radicals Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract 2
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- -1 alkylene radical Chemical class 0.000 abstract 1
- 150000001409 amidines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Procedure for the preparation of new amidines of formula: **(See formula)** where R is fixed in the ortho, mete or para position relative to Z and represents a terpenic radical, of exo or endo configuration, 2-isobornyl, 5-isocanyl or 2-norbornyl, R'and R''are the same or different and each represent a hydrogen or halogen atom, a straight or branched chain alkyl or alkoxy group of 1 to 4 carbon atoms, or a nitro or cyano group, Z is a single bond or an oxygen or sulfur, A is a straight chain or branched alkylene radical having 1 to 4 carbon atoms or the radical -CH2-CHOH-CH2-, R1 is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, hydroxyethyl or benzyl, R2 and R3 are hydrogen atoms or together represent a radical -CH2-CH3- or -CH2-CH2-CH2, thus forming with the radical (see formula) to which a Δ 2-imidazoline cycle is linked or 1,4,5,6-tetrahydropyrimidine, characterized in that it consists of reacting, in an alcoholic medium, a compound of the formula: **(See formula)** where R, R', R'', Z and A have the same meanings as in formula (I), with ammonia, ethylenediamine or 1,3-diamino-propane and eventually subjecting the compound obtained to an alkylation. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2656375A GB1548875A (en) | 1975-06-23 | 1975-06-23 | Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES449161A1 true ES449161A1 (en) | 1977-12-01 |
Family
ID=10245609
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES449161A Expired ES449161A1 (en) | 1975-06-23 | 1976-06-23 | Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions |
| ES461262A Expired ES461262A1 (en) | 1975-06-23 | 1977-08-01 | Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES461262A Expired ES461262A1 (en) | 1975-06-23 | 1977-08-01 | Terpnyl phen (oxy)elkyl amideines and their use in pharmaceutical compositions |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE843255A (en) |
| CH (3) | CH614932A5 (en) |
| ES (2) | ES449161A1 (en) |
| FR (1) | FR2315259A1 (en) |
| GB (1) | GB1548875A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2469405A1 (en) * | 1979-11-16 | 1981-05-22 | Ugine Kuhlmann | Systemic fungicidal salicylic acid ester(s) - 3,4,5,6-tetra:hydro:pyrimidin-2-yl-methyl and 2-imidazolin-2-yl methyl esters of 5-methyl 3-norbornyl-(2) salicylic acid |
| MX2009013742A (en) * | 2007-07-02 | 2010-01-26 | Hoffmann La Roche | 2 -imidazolines having a good affinity to the trace amine associated receptors (taars). |
| MX355972B (en) | 2009-11-19 | 2018-05-07 | Yissum Res Dev Co Of Hebrew Univ Jerusalem Ltd | Novel arylated camphenes, processes for their preparation and uses thereof. |
| WO2012044719A1 (en) | 2010-09-28 | 2012-04-05 | Promerus Llc | Norbornane-based pac ballast and positive-tone photosensitive resin composition encompassing the pac |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1317514A (en) * | 1970-11-30 | 1973-05-23 | Erba Carlo Spa | Imidazoline derivatives |
| GB1504862A (en) * | 1974-04-11 | 1978-03-22 | Mar Pha Etu Expl Marques | Terpeno-phenoxyalkylamines |
-
1975
- 1975-06-23 GB GB2656375A patent/GB1548875A/en not_active Expired
-
1976
- 1976-06-11 FR FR7617713A patent/FR2315259A1/en active Granted
- 1976-06-21 CH CH789576A patent/CH614932A5/en not_active IP Right Cessation
- 1976-06-22 BE BE168187A patent/BE843255A/en not_active IP Right Cessation
- 1976-06-23 ES ES449161A patent/ES449161A1/en not_active Expired
-
1977
- 1977-08-01 ES ES461262A patent/ES461262A1/en not_active Expired
-
1979
- 1979-01-30 CH CH90279A patent/CH614941A5/en not_active IP Right Cessation
- 1979-01-30 CH CH90179A patent/CH614940A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH614940A5 (en) | 1979-12-28 |
| CH614941A5 (en) | 1979-12-28 |
| GB1548875A (en) | 1979-07-18 |
| CH614932A5 (en) | 1979-12-28 |
| ES461262A1 (en) | 1978-05-01 |
| BE843255A (en) | 1976-12-22 |
| FR2315259A1 (en) | 1977-01-21 |
| FR2315259B1 (en) | 1978-12-08 |
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