IE33387B1 - Novel cyclic amidines and the therapeutic use thereof - Google Patents
Novel cyclic amidines and the therapeutic use thereofInfo
- Publication number
- IE33387B1 IE33387B1 IE147/69A IE14769A IE33387B1 IE 33387 B1 IE33387 B1 IE 33387B1 IE 147/69 A IE147/69 A IE 147/69A IE 14769 A IE14769 A IE 14769A IE 33387 B1 IE33387 B1 IE 33387B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- general formula
- ring
- atom
- prepared
- Prior art date
Links
- -1 cyclic amidines Chemical class 0.000 title abstract 11
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 230000005494 condensation Effects 0.000 abstract 5
- 238000009833 condensation Methods 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 abstract 1
- FJSZMLXMZBXPLB-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-cyanoethanethioamide Chemical compound ClC1=CC=C(C=C1)C(C(=S)N)C#N FJSZMLXMZBXPLB-UHFFFAOYSA-N 0.000 abstract 1
- NMRRHBBUTOXXPH-UHFFFAOYSA-N 2-(4-chlorophenyl)propanedinitrile Chemical compound ClC1=CC=C(C(C#N)C#N)C=C1 NMRRHBBUTOXXPH-UHFFFAOYSA-N 0.000 abstract 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 abstract 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 150000002485 inorganic esters Chemical group 0.000 abstract 1
- 229940118019 malondialdehyde Drugs 0.000 abstract 1
- VFOJMKRYKVNVGA-UHFFFAOYSA-N methyl(phenyl)cyanamide Chemical compound N#CN(C)C1=CC=CC=C1 VFOJMKRYKVNVGA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002895 organic esters Chemical class 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Float Valves (AREA)
- Self-Closing Valves And Venting Or Aerating Valves (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70426368A | 1968-02-09 | 1968-02-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33387L IE33387L (en) | 1969-08-09 |
| IE33387B1 true IE33387B1 (en) | 1974-06-12 |
Family
ID=24828765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE147/69A IE33387B1 (en) | 1968-02-09 | 1969-02-04 | Novel cyclic amidines and the therapeutic use thereof |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5114514B1 (en)) |
| AT (2) | AT294819B (en)) |
| BE (1) | BE727951A (en)) |
| BR (1) | BR6906150D0 (en)) |
| CA (1) | CA941829A (en)) |
| CH (1) | CH515254A (en)) |
| CS (2) | CS154613B2 (en)) |
| DE (1) | DE1905353C3 (en)) |
| ES (1) | ES363246A0 (en)) |
| FR (1) | FR2001655A1 (en)) |
| GB (1) | GB1259005A (en)) |
| IE (1) | IE33387B1 (en)) |
| IL (1) | IL31555A (en)) |
| LU (1) | LU57890A1 (en)) |
| NL (1) | NL6901741A (en)) |
| NO (1) | NO126228B (en)) |
| SE (1) | SE372946B (en)) |
| SU (1) | SU365883A3 (en)) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965112A (en) * | 1971-01-11 | 1976-06-22 | John Wyeth & Brother Limited | Imidazoline derivatives |
| JPS5329010A (en) * | 1976-08-30 | 1978-03-17 | Gen Res Electronics Inc | Cb transceiver with broadcasting band radio receiver |
| JPS53137721U (en)) * | 1977-04-07 | 1978-10-31 | ||
| JPS5861552U (ja) * | 1981-10-19 | 1983-04-25 | ソニー株式会社 | 受信機 |
| JPS59143431A (ja) * | 1983-02-03 | 1984-08-17 | Sony Corp | 無線機 |
| GB2351082A (en) * | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Synthesis of Cyclic Substituted Amidines |
| FR2846328B1 (fr) * | 2002-10-23 | 2004-12-10 | Servier Lab | Nouveaux derives de l'imidazoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
-
1969
- 1969-02-04 IE IE147/69A patent/IE33387B1/xx unknown
- 1969-02-04 IL IL31555A patent/IL31555A/xx unknown
- 1969-02-04 LU LU57890D patent/LU57890A1/xx unknown
- 1969-02-04 NL NL6901741A patent/NL6901741A/xx not_active Application Discontinuation
- 1969-02-04 ES ES363246A patent/ES363246A0/es active Pending
- 1969-02-04 NO NO00408/69*[A patent/NO126228B/no unknown
- 1969-02-04 AT AT426370A patent/AT294819B/de not_active IP Right Cessation
- 1969-02-04 DE DE1905353A patent/DE1905353C3/de not_active Expired
- 1969-02-04 CH CH179369A patent/CH515254A/de not_active IP Right Cessation
- 1969-02-04 GB GB1259005D patent/GB1259005A/en not_active Expired
- 1969-02-04 CA CA042,002A patent/CA941829A/en not_active Expired
- 1969-02-04 AT AT426470A patent/AT295520B/de not_active IP Right Cessation
- 1969-02-05 BR BR206150/69A patent/BR6906150D0/pt unknown
- 1969-02-05 SE SE6901538A patent/SE372946B/xx unknown
- 1969-02-05 JP JP44008194A patent/JPS5114514B1/ja active Pending
- 1969-02-05 BE BE727951D patent/BE727951A/xx unknown
- 1969-02-07 SU SU1315880A patent/SU365883A3/ru active
- 1969-02-07 CS CS580070A patent/CS154613B2/cs unknown
- 1969-02-07 CS CS580170A patent/CS154614B2/cs unknown
- 1969-02-07 FR FR6902936A patent/FR2001655A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1259005A (en)) | 1972-01-05 |
| DE1905353A1 (de) | 1969-09-04 |
| CS154613B2 (en)) | 1974-04-30 |
| BE727951A (en)) | 1969-08-05 |
| SU365883A3 (en)) | 1973-01-08 |
| IL31555A0 (en) | 1969-04-30 |
| ES363246A0 (es) | 1971-01-16 |
| JPS5114514B1 (en)) | 1976-05-10 |
| SE372946B (en)) | 1975-01-20 |
| AT295520B (de) | 1972-01-10 |
| BR6906150D0 (pt) | 1973-04-12 |
| NL6901741A (en)) | 1969-08-12 |
| AT294819B (de) | 1971-12-10 |
| CH515254A (de) | 1971-11-15 |
| IE33387L (en) | 1969-08-09 |
| CA941829A (en) | 1974-02-12 |
| DE1905353C3 (de) | 1979-08-30 |
| CS154614B2 (en)) | 1974-04-30 |
| FR2001655A1 (en)) | 1969-09-26 |
| DE1905353B2 (de) | 1978-12-21 |
| LU57890A1 (en)) | 1969-05-04 |
| NO126228B (en)) | 1973-01-08 |
| IL31555A (en) | 1972-10-29 |
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