IE32417B1 - Guanidines - Google Patents
GuanidinesInfo
- Publication number
- IE32417B1 IE32417B1 IE1223/68A IE122368A IE32417B1 IE 32417 B1 IE32417 B1 IE 32417B1 IE 1223/68 A IE1223/68 A IE 1223/68A IE 122368 A IE122368 A IE 122368A IE 32417 B1 IE32417 B1 IE 32417B1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- compounds
- prepared
- ethoxy
- reacting
- Prior art date
Links
- 150000002357 guanidines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract 1
- PAWIXECATDEZRE-UHFFFAOYSA-N 2,4,6-trichloro-3-ethoxybenzaldehyde Chemical class C(C)OC=1C(=C(C=O)C(=CC1Cl)Cl)Cl PAWIXECATDEZRE-UHFFFAOYSA-N 0.000 abstract 1
- WDZVGELJXXEGPV-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methylideneamino]guanidine Chemical compound NC(N)=NN=CC1=C(Cl)C=CC=C1Cl WDZVGELJXXEGPV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 230000000891 anti-reserpine Effects 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003345 hyperglycaemic effect Effects 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960005181 morphine Drugs 0.000 abstract 1
- 230000002911 mydriatic effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 230000003236 psychic effect Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,223,491. Aminoguanidine derivatives. AMERICAN HOME PRODUCTS CORP. 22 Feb., 1968 [13 Oct., 1967], No. 8629/68. Heading C2C. The invention comprises compounds of formula and their acid-addition salts, wherein X is a direct bond, CH 2 , CH 2 CH 2 or CH: CH; R<SP>1</SP>, R<SP>2</SP> and Y are each halogen, NO 2 , amino, alkylsubstituted amino, alkyl, alkoxy, benzyloxy (possibly halogen-substituted), OH or CF 3 , n is 0, 1, 2 or 3 (or n is 1 and Y+R<SP>2</SP> form together O-CH 2 -O), R<SP>3</SP> is H, C 3-5 cycloalkyl, alkyl, ethynyl, allyl or benzyl, and R<SP>4</SP>, R<SP>5</SP>, R<SP>6</SP> are each H or alkyl (or when R<SP>6</SP> is H, then R<SP>4</SP>, R<SP>5</SP> and the attached N atoms may form an imidazoline ring), the alkyl and alkoxy groups containing 1-6 C atoms, but excluding 2,6-dichlorobenzylideneaminoguanidine (A). These compounds are prepared by reacting the corresponding carbonyl compound (B) with an aminoguanidine or its salt, or by heating B-thiosemicarbazone with NH 3 , or by reacting B-hydrazone with CNNH 2 . Starting materials.-2,5-Dibromopropiophenone and 2,5-dichlorobutyrophenone are prepared by a Friedel-Crafts reaction. 2,6-Dichloro-3- ethoxy- and 2,4,6-trichloro-3-ethoxy-benzaldehydes are prepared from the 3-hydroxy compounds with Et 2 SO 4 + K 2 CO 3 . Pharmaceutical and veterinary compositions for oral or parenteral administration comprise compounds of the above formula (including A), which have hypotensive, antihypertensive, antibacterial, CNS (e.g. anti-reserpine, anti-morphine, anti-oxytremorine, depressant or mydriatic), analgesic, diuretic, hyperglycaemic, anti-inflammatory, anorectic, stimulant, psychic energizing, tranquilizing and anti-Parkinson activity.
[GB1223491A]
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE1363/71A IE32852B1 (en) | 1967-10-13 | 1968-10-14 | Guanidines |
| IE1364/71A IE32853B1 (en) | 1968-02-22 | 1968-10-14 | Guanidines |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67502667A | 1967-10-13 | 1967-10-13 | |
| GB8629/68A GB1223491A (en) | 1967-10-13 | 1968-02-22 | Guanidines |
| US75449468A | 1968-08-21 | 1968-08-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32417L IE32417L (en) | 1969-04-13 |
| IE32417B1 true IE32417B1 (en) | 1973-07-25 |
Family
ID=27255238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1223/68A IE32417B1 (en) | 1967-10-13 | 1968-10-14 | Guanidines |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE722136A (en) |
| CA (2) | CA958018A (en) |
| CH (2) | CH560188A5 (en) |
| DE (1) | DE1802394C2 (en) |
| DK (1) | DK128350B (en) |
| FI (1) | FI49958C (en) |
| GB (2) | GB1223492A (en) |
| IE (1) | IE32417B1 (en) |
| IL (1) | IL30782A (en) |
| IT (1) | IT1062053B (en) |
| NL (1) | NL166014C (en) |
| PH (1) | PH10262A (en) |
| SE (1) | SE381041B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH523232A (en) * | 1968-12-16 | 1972-05-31 | Sandoz Ag | Process for the preparation of a benzylidene aminoguanidine |
| US4006249A (en) | 1975-08-06 | 1977-02-01 | American Home Products Corporation | Systemic treatment of psoriasis |
| EP0021120B1 (en) * | 1979-06-01 | 1983-04-06 | The Wellcome Foundation Limited | 3,5-diamino-1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them |
| JPS5625169A (en) * | 1979-06-01 | 1981-03-10 | Wellcome Found | Triazine derivative |
| DE3360148D1 (en) * | 1982-02-10 | 1985-06-05 | Beecham Group Plc | Guanidine derivatives |
| FR2669927B1 (en) * | 1990-11-29 | 1994-04-08 | Adir Cie | NOVEL GUANIDINE DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| GB2277090A (en) * | 1993-04-16 | 1994-10-19 | Shell Int Research | Fungicidal tetrahydropyrimidine and imidazoline derivatives |
| SE9604348D0 (en) | 1996-11-26 | 1996-11-26 | Wapharm Ab | Use of hydroxyguanidines |
| AU7802700A (en) * | 1999-10-06 | 2001-05-10 | Melacure Therapeutics Ab | Guanidine derivatives and their use in the production of a medicament for blocking xanthine oxidase/dehydrogenase |
| GB0019357D0 (en) | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel phenyl guanidines |
| GB0108631D0 (en) * | 2001-04-05 | 2001-05-30 | Melacure Therapeutics Ab | Novel benzylideneamino guanidines and their uses as ligands to the melanocortin receptors |
| DE10149919A1 (en) | 2001-10-10 | 2003-04-24 | Biosphings Ag | New carboxylic acid salts of guanidine derivatives useful as sphingomyelinase inhibitors for treating e.g. tumor, cardiovascular or viral diseases |
| FR2893844B1 (en) | 2005-11-28 | 2008-02-01 | Centre Nat Rech Scient | USE OF GUANABENZ AND ITS DERIVATIVES FOR THE MANUFACTURE OF MEDICAMENTS FOR THE TREATMENT OF MUCOVISCIDOSIS AND DISEASES ASSOCIATED WITH A DEFECT OF ADDRESSING PROTEINS IN CELLS |
| GB0624987D0 (en) | 2006-12-14 | 2007-01-24 | Acure Pharma Ab | Novel aminoguanidines as melanocortin receptor ligands |
| GB201300435D0 (en) * | 2013-01-10 | 2013-02-27 | Medical Res Council | Benzylideneguanidine Derivatives and Therapeutic Use for the Treatment of Protein Misfolding Diseases |
| KR102572217B1 (en) | 2015-04-08 | 2023-08-28 | 유나이티드 킹덤 리서치 앤드 이노베이션 | Methods for screening phosphatase selective and non-selective phosphatase inhibitors |
| EP3109237A1 (en) * | 2015-06-22 | 2016-12-28 | AnaMar AB | Novel 5-ht2 antagonists |
| US11166464B2 (en) * | 2017-03-06 | 2021-11-09 | The United States Of America, As Represented By The Secretary Of Agriculture | Self-assembled active agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958832C (en) * | 1952-11-14 | 1957-02-28 | Bayer Ag | Process for the preparation of guanylhydrazones |
| GB1019120A (en) * | 1964-03-18 | 1966-02-02 | Shell Int Research | Novel hydrazine compounds and compositions containing them |
-
1968
- 1968-02-22 GB GB39073/70A patent/GB1223492A/en not_active Expired
- 1968-02-22 GB GB8629/68A patent/GB1223491A/en not_active Expired
- 1968-09-29 IL IL30782A patent/IL30782A/en unknown
- 1968-10-04 IT IT22075/68A patent/IT1062053B/en active
- 1968-10-07 PH PH9625A patent/PH10262A/en unknown
- 1968-10-10 DE DE1802394A patent/DE1802394C2/en not_active Expired
- 1968-10-10 BE BE722136D patent/BE722136A/xx not_active IP Right Cessation
- 1968-10-11 DK DK492468AA patent/DK128350B/en not_active IP Right Cessation
- 1968-10-11 NL NL6814608.A patent/NL166014C/en not_active IP Right Cessation
- 1968-10-11 SE SE6813751A patent/SE381041B/en unknown
- 1968-10-11 FI FI682889A patent/FI49958C/en active
- 1968-10-12 CA CA032,413A patent/CA958018A/en not_active Expired
- 1968-10-14 IE IE1223/68A patent/IE32417B1/en unknown
- 1968-10-14 CH CH1534368A patent/CH560188A5/xx not_active IP Right Cessation
- 1968-10-14 CH CH119372A patent/CH524577A/en not_active IP Right Cessation
-
1971
- 1971-06-17 CA CA115885A patent/CA921829A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH524577A (en) | 1972-06-30 |
| CA921829A (en) | 1973-02-27 |
| DE1802394A1 (en) | 1969-05-08 |
| GB1223492A (en) | 1971-02-24 |
| NL166014B (en) | 1981-01-15 |
| FI49958B (en) | 1975-07-31 |
| IT1062053B (en) | 1983-06-25 |
| IL30782A (en) | 1972-08-30 |
| SE381041B (en) | 1975-11-24 |
| NL166014C (en) | 1981-06-15 |
| DE1802394C2 (en) | 1984-06-28 |
| GB1223491A (en) | 1971-02-24 |
| NL6814608A (en) | 1969-04-15 |
| CH560188A5 (en) | 1975-03-27 |
| BE722136A (en) | 1969-04-10 |
| IE32417L (en) | 1969-04-13 |
| PH10262A (en) | 1976-10-20 |
| DK128350B (en) | 1974-04-16 |
| CA958018A (en) | 1974-11-19 |
| FI49958C (en) | 1975-11-10 |
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