ES424483A1 - Hererocyclic derivatives of a guanidine - Google Patents
Hererocyclic derivatives of a guanidineInfo
- Publication number
- ES424483A1 ES424483A1 ES424483A ES424483A ES424483A1 ES 424483 A1 ES424483 A1 ES 424483A1 ES 424483 A ES424483 A ES 424483A ES 424483 A ES424483 A ES 424483A ES 424483 A1 ES424483 A1 ES 424483A1
- Authority
- ES
- Spain
- Prior art keywords
- radical
- carbon atoms
- lower alcohol
- straight
- atoms
- 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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title 1
- -1 guanidinylidene radical Chemical class 0.000 abstract 15
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 3
- 150000003254 radicals Chemical class 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 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
-
- 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
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
-
- 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
- C07D239/08—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 with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/16—Nitrogen atoms not forming part of a nitro radical acylated on said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Procedure for the preparation of heterocyclic compounds substituted by a guanidinylidene radical of the general formula I **(See formula)** wherein R1 and R2 signify hydrogen atoms or straight or branched lower alcohol radicals with 1 to 4 carbon atoms and one of these radicals also signifies a hydroxyl group; R3 and R4 signify hydrogen atoms or straight or branched lower alcohol radicals with 1 to 4 carbon atoms; R5 signifies a hydrogen atom, a straight or branched lower alcohol radical with 1 to 6 carbon atoms, a hydroxyalkyl radical with 2 or 3 carbon atoms, a phenyl radical, optionally monosubstituted or substituted by lower alcohol or alkoxy radicals with 1 to 2 carbon atoms, by fluorine, chlorine or bromine atoms, or by nitrile groups, a benzyl or phenylethyl radical optionally monosubstituted or disubstituted by halogen atoms or the adamantyl radical; R6 signifies a hydrogen atom or a straight or branched chain lower alcohol radical with 1 to 4 carbon atoms; R7 signifies a hydrogen atom, a straight or branched lower alcohol radical with 1 to 6 carbon atoms, a hydroxyalkyl radical with 2 or 3 carbon atoms, a benzyl or phenethyl radical optionally substituted by halogen atoms, with alcohol radicals or lower alkoxy with 1 6 2 carbon atoms, a phenyl radical optionally substituted by chlorine atoms, carboxyl or aminosulfonyl groups, or an adamantyl radical; R8 means a hydrogen atom, a straight or branched chain lower alcohol radical with 1 to 4 carbon atoms or together with R7 and the nitrogen atom located between them mean a saturated 5- to 7-membered heterocyclic ring, which is eventually interrupted by an oxygen or sulfur atom or by another nitrogen atom, which may be substituted by a lower alcohol radical or a phenyl radical, and n denotes 0 or 1, as well as its acid addition salts physiologically compatible with organic or inorganic acids, characterized in that an S-alcoholylthiourea of the general formula II is reacted **(See formula)** wherein the radicals R1 through R5 are defined as indicated above and the radical R9 represents an alcoholic group, or its salts with organic or inorganic acids, with an amine of the general formula III (see formula) (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205744A DE2205744A1 (en) | 1972-02-08 | 1972-02-08 | Guanidinylidene-subst cpds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES424483A1 true ES424483A1 (en) | 1976-06-16 |
Family
ID=5835294
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES411341A Expired ES411341A1 (en) | 1972-02-08 | 1973-02-06 | Hererocyclic derivatives of a guanidine |
| ES424483A Expired ES424483A1 (en) | 1972-02-08 | 1974-03-21 | Hererocyclic derivatives of a guanidine |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES411341A Expired ES411341A1 (en) | 1972-02-08 | 1973-02-06 | Hererocyclic derivatives of a guanidine |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4891068A (en) |
| AT (2) | AT319268B (en) |
| AU (1) | AU472170B2 (en) |
| BE (1) | BE795112A (en) |
| DE (1) | DE2205744A1 (en) |
| ES (2) | ES411341A1 (en) |
| FR (1) | FR2181714B1 (en) |
| GB (1) | GB1409768A (en) |
| NL (1) | NL7301701A (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ183570A (en) * | 1976-03-19 | 1979-06-08 | Mcneilab Inc | Heterocyclic guanidine derivatives, having anti-secretory and hypogliycaemic activity |
| US4211867A (en) | 1976-03-19 | 1980-07-08 | Mcneil Laboratories, Incorporated | Nitrogen heterocyclic carboximidamide compounds |
| US4266062A (en) | 1978-09-18 | 1981-05-05 | Mcneilab, Inc. | (1-Methyl-2-pyridinylidene) derivatives of guanidine |
| US4414211A (en) | 1978-09-18 | 1983-11-08 | Mcneilab, Inc. | Heterocyclic derivatives of guanidine |
| CA1201119A (en) * | 1978-09-18 | 1986-02-25 | Mcneilab, Inc. | Diaza-cyclic derivatives of guanidine |
| US4182865A (en) * | 1978-09-18 | 1980-01-08 | Mcneil Laboratories, Inc. | Diaza-cyclic derivatives of guanidine |
| AU5263779A (en) * | 1978-11-29 | 1980-05-29 | Beecham Group Limited | Derivatives of thiazolidin-2-ylidene and oxazolidin-2-ylidene with hypoglycaemic acitivity |
| DE3061396D1 (en) | 1979-04-20 | 1983-01-27 | Beecham Group Plc | Oxazoline and thiazoline derivatives, processes for their preparation and pharmaceutical compositions containing them |
| EP0020304A1 (en) * | 1979-05-29 | 1980-12-10 | Ciba-Geigy Ag | Guanidines, process for their preparation, pharmaceutical preparations containing such compounds and their application |
| JPS55160764A (en) * | 1979-05-29 | 1980-12-13 | Ciba Geigy Ag | Guanidine* its manufacture and pharmaceutic medicine containing same |
| EP0034002A3 (en) * | 1980-01-22 | 1981-09-23 | Beecham Group Plc | Carboxamidine derivatives |
| DE102004008141A1 (en) | 2004-02-19 | 2005-09-01 | Abbott Gmbh & Co. Kg | Guanidine compounds and their use as binding partners for 5-HT5 receptors |
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
-
1972
- 1972-02-08 DE DE2205744A patent/DE2205744A1/en active Pending
-
1973
- 1973-02-06 ES ES411341A patent/ES411341A1/en not_active Expired
- 1973-02-07 AU AU51928/73A patent/AU472170B2/en not_active Expired
- 1973-02-07 BE BE795112D patent/BE795112A/en unknown
- 1973-02-07 JP JP48015457A patent/JPS4891068A/ja active Pending
- 1973-02-07 AT AT107173A patent/AT319268B/en not_active IP Right Cessation
- 1973-02-07 GB GB607273A patent/GB1409768A/en not_active Expired
- 1973-02-07 NL NL7301701A patent/NL7301701A/xx unknown
- 1973-02-07 AT AT1061673A patent/AT324351B/en not_active IP Right Cessation
- 1973-02-08 FR FR7304496A patent/FR2181714B1/fr not_active Expired
-
1974
- 1974-03-21 ES ES424483A patent/ES424483A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181714A1 (en) | 1973-12-07 |
| GB1409768A (en) | 1975-10-15 |
| AT319268B (en) | 1974-12-10 |
| DE2205744A1 (en) | 1973-08-09 |
| AT324351B (en) | 1975-08-25 |
| AU472170B2 (en) | 1976-05-20 |
| NL7301701A (en) | 1973-08-10 |
| ES411341A1 (en) | 1976-03-16 |
| JPS4891068A (en) | 1973-11-27 |
| FR2181714B1 (en) | 1977-07-01 |
| AU5192873A (en) | 1974-08-08 |
| BE795112A (en) | 1973-08-07 |
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