US3409669A - 2-(cyclohexylamino)-2-methyl-propylguanidine-1 and the salts and hydrate thereof - Google Patents
2-(cyclohexylamino)-2-methyl-propylguanidine-1 and the salts and hydrate thereof Download PDFInfo
- Publication number
- US3409669A US3409669A US413315A US41331564A US3409669A US 3409669 A US3409669 A US 3409669A US 413315 A US413315 A US 413315A US 41331564 A US41331564 A US 41331564A US 3409669 A US3409669 A US 3409669A
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- United States
- Prior art keywords
- grams
- methyl
- cyclohexylamino
- water
- solution
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- 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 - Lifetime
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Definitions
- R represents a cycloalkyl group of from 5 to 7 carbo
- R represents a cycloalkyl group of from 5 to 7 carbo
- certain guanidine compounds which are described in detail below, possess particularly especially against renal and According to the present invention we provide compounds of the general formula R N-R I R-NH-o-cm-NH-c R2 I'd-R5 and their hydrates and with one or more alkyl groups having 1-4 carbon atoms.
- R is a hydrogen atom or an alkyl group having 1-4 carbon atoms.
- R is an alkyl group having 1-4 carbon atoms.
- R R and R which may be the same or different, are hydrogen atoms or alkyl groups having 1-4 carbon atoms.
- R is methyl and R is hydrogen or methyl.
- R R is cyclohexyl and R R and R cial y noteworthy in this respect.
- R R and/or R is an alkyl group thismay, be a straight chained or branched chained alkyl group, e.g. a methyl, ethyl, butyl group etc.
- the compounds exist as optical isomers and racemic mixtures and zoates, salicylates, nates, p-toluene sulphonates etc.
- the new guanidines according to the invention may be emulsifyture of the invention, there is provided a process for the preparation of compounds of the general formula meanings and R is is reacted, where R tive of the general formula N-R3 a s- (where R is an alkyl or aralkyl group, atom or an alkyl group having and R have the above meanings) or a salt thereof, with cyanamide, with N-nitrosoguanidine with an N-alkyl-N- nitrosoguanidine or with a cyanogen halide followed by reaction of the cyanogen-halide-reaction product with ammonia or an amine, or is reacted, where R is a group with mercuric oxide and ammonia or an amine.
- the salt of the thiourea derivative may, for example, be a mineral acid salt such as a hydrohalide, nitrate or sulphate.
- the reaction with the thiourea derivative may be effected in the presence or absence of a solvent, suitable solvents, where present, including water and watermiscible organic solvents such as water miscible alcohols, ethers, ketones, or carboxylic acids, e.g. methanol, ethanol, propanol, dioxan, tetrahydrofuran, acetone, methyl ethyl ketone, acetic acid etc.
- the reaction temperature is not especially critical and normal temperature is generally convenient, although higher temperatures, e.g. up to the boiling point of the medium, can also be used.
- the compounds of Formula I as defined above can be prepared by reacting the compound of Formula II wherein R is hydrogen with a compound of the general formula R is a hydrogen 1-4 carbon atoms and R and R R and salt thereof.
- the amines of general Formula II used in the above methods can be conveniently prepared by reduction of the corresponding nitriles of the general formula
- the above nitriles can be prepared, for example, by condensation of an amine RNI-I with an aldehyde or ketone R CO--R followed by treatment with a cyanide.
- the aldehyde or ketone is preferably in the form of its bisulphite adduct, e.g. sodium acetaldehyde bisulphite, sodium acetone bisulphite etc.
- the cycloalkyl amine is advantageously added dropwise to a solution of the bisulphite adduct in an aqueous solvent such as water.
- the cyanide is preferably an alkali metal cyanide, e.g. sodium, potassium cyanide etc.
- the amine RNH may be condensed with a cyanhydrin of the aldehyde in ketone R ---COR to give the nitrile directly.
- the reduction of the nitrile is preferably effected with a metal hydride reducing agent, e.g. lithium aluminium hydride in a solvent medium e.g. ether or tetrahydrofuran.
- a metal hydride reducing agent e.g. lithium aluminium hydride in a solvent medium e.g. ether or tetrahydrofuran.
- the amines of Formula II above may also be prepared by condensation of a cycloalkanone with a diamine followed by reduction of the resulting Schiffs base.
- the substituents R R and R may be introduced subsequently, by alkylation, for example using conventional techniques such as reaction with an alkyl halide, sulphate or aromatic-sulphonate alkylating agent.
- the methods of preparation of the new compounds described herein will in general give rise to the compounds in the form of salts.
- the free base may be prepared from the salt by treatment with a strong anion exchange resin or treatment with caustic alkali or silver oxide.
- Other salts may be formed from the free base so obtained.
- conventional ion exchange techniques may be used, e.g. using anion exchange resin.
- the 2-(cyclohexylamine)propylamine used in the above preparation was made as follows: Sodium acetaldehyde bisulphite (364 grams) was dissolved in water (800 millilitres) and to the solution, cyclohexylamine (198 grams) was added dropwise at room temperature during the course of thirty minutes, with mechanical stirring. The mixture was allowed to stand for a further one hour after which it was treated with a solution of sodium by evaporation and the product 2-(cyclohexylamino) propylamine distilled at reduced pressure. It has B.P. 105-7/18 mm., and n 1.4742. Yield 122 grams.
- EXAMPLE 2 A mixture of S-methylisothiourea sulphate (15.8 grams), 2-cyclohexylamino-Z-methyl-propylamine 16.6 grams) and water (50 millilitres) was allowed to stand overnight at room temperature. The evolution of methyl mercaptan was completed by heating the solution on a water bath for another hour. After cooling, the crystals of 2-cyclohexylamino-2-methyl-propylguanidine sulphate which had separated, were recrystallised from a mixture of alcohol and water and had M.P. 203-6 C. Yield 18 grams.
- the 2-cyclohexylamino-2-methyl-propylamine required was prepared in the following way: A solution of 120 grams of acetone sodium bisulphite in 400 millilitres of water was slowly treated with 66 grams of cyclohexylamine. After standing for one hour the mixture was treated with 36 grams of sodium cyanide dissolved in 70 millilitres of water. The upper layer of 2-cyclohexylamino-2-methyl-propionitrile which formed was removed, and the lower layer extracted three times with ether. The ether extracts were combined and added to the original upper layer of nitrile. The other solution so obtained was dried over anhydrous sodium sulphate. The residue, after removal of the yield 47 grams standing, and had M.P. 52 C.
- EXAMPLE 3 A solution of sodium propionaldehyde bisulphite was prepared by careful addition, with ice cooling, of propionaldehyde (58 grams) to aqueous sodium bisulphite (300 millilitres of 37%). To the solution, cyclohexylamine (99 grams) was added dropwise during the course of. 30 minutes at room temperature under mechanical stirring which was continued for a further 60 minutes. A solution of sodium cyanide (100 grams) in water (200 millilitres) was then added and the resultant mixture was stirred for a further 3 hours and then allowed to stand overnight. The so formed. 2-cyclo-hexylamino-nbutyronitrile was extracted with ether and the ether extract dried over anhydrous sodium sulphate.
- the active ingredient in this composition is 2-(cyclohexylamino)propylguanidine sulphate or 2-(cyclohexylamino)-2-methyl propylguanidine sulphate.
- EXAMPLE 6INJECTION (10 MG./ML.) Formula Active ingredient Water for injection B.P. to 100 ml.
- the active ingredient was dissolved in the sulphuric acid which had previously been made up to 70 ml. with water for injection. After adjusting the pH to 7.4 with the sodium hydroxide, the solution was made up to 100 ml. for ln ection and sterilised by filtration through a /3 sintered glass filter or a sterilising grade membrane filter before being aseptically packed in sterile 1 ml. ampoules.
- the active ingredient in this composition is 2-(cycl0- hexylamino)propylguanidine sulphate, or 2-(cyclohcxylamino)-2-methyl propylguanidine sulphate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB49408/63A GB1110947A (en) | 1963-12-13 | 1963-12-13 | Guanidines |
Publications (1)
Publication Number | Publication Date |
---|---|
US3409669A true US3409669A (en) | 1968-11-05 |
Family
ID=10452240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US413315A Expired - Lifetime US3409669A (en) | 1963-12-13 | 1964-11-23 | 2-(cyclohexylamino)-2-methyl-propylguanidine-1 and the salts and hydrate thereof |
Country Status (8)
Country | Link |
---|---|
US (1) | US3409669A (is) |
BE (1) | BE656923A (is) |
CH (1) | CH471071A (is) |
DE (1) | DE1214674B (is) |
FR (1) | FR3889M (is) |
GB (1) | GB1110947A (is) |
NL (1) | NL6413937A (is) |
SE (1) | SE331090B (is) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6025355A (en) * | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
US6251948B1 (en) | 1990-03-02 | 2001-06-26 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US6756389B2 (en) | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3291829A (en) * | 1961-03-02 | 1966-12-13 | Ciba Geigy Corp | Alkyl guanidines |
-
1963
- 1963-12-13 GB GB49408/63A patent/GB1110947A/en not_active Expired
-
1964
- 1964-05-22 DE DEE27090A patent/DE1214674B/de active Pending
- 1964-11-23 US US413315A patent/US3409669A/en not_active Expired - Lifetime
- 1964-11-30 CH CH1540864A patent/CH471071A/de not_active IP Right Cessation
- 1964-12-01 NL NL6413937A patent/NL6413937A/xx unknown
- 1964-12-08 FR FR997779A patent/FR3889M/fr not_active Expired
- 1964-12-10 BE BE656923D patent/BE656923A/xx unknown
- 1964-12-11 SE SE14996/64A patent/SE331090B/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3291829A (en) * | 1961-03-02 | 1966-12-13 | Ciba Geigy Corp | Alkyl guanidines |
Cited By (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
US5478863A (en) * | 1986-07-10 | 1995-12-26 | State Of Oregon, Oregon Health Sciences University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5604228A (en) * | 1986-07-10 | 1997-02-18 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5767162A (en) * | 1990-03-02 | 1998-06-16 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5336689A (en) * | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US6251948B1 (en) | 1990-03-02 | 2001-06-26 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5559154A (en) * | 1990-03-02 | 1996-09-24 | Oregon State Board Of Higher Education | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5798390A (en) * | 1990-03-02 | 1998-08-25 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5637622A (en) * | 1990-03-02 | 1997-06-10 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
US5837737A (en) * | 1991-02-08 | 1998-11-17 | Cambridge Neuroscience, Inc. | Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same |
US5622968A (en) * | 1991-02-08 | 1997-04-22 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
US5670519A (en) * | 1991-02-08 | 1997-09-23 | Cambridge Neuroscience, Inc. | Acenaphthyl-substituted guanidines and methods of use thereof |
US5672608A (en) * | 1991-02-08 | 1997-09-30 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
US5677348A (en) * | 1991-02-08 | 1997-10-14 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
US5681861A (en) * | 1991-02-08 | 1997-10-28 | Cambridge Neuroscience, Inc. | Aminoguanidines and methods of use of same |
US5686495A (en) * | 1991-02-08 | 1997-11-11 | Cambridge Neuroscience, Inc. | Substituted hydrazinedicarboximidamides and methods of use thereof |
US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US5637623A (en) * | 1991-02-08 | 1997-06-10 | Cambridge Neuroscience, Inc. | Substituted adamantyl guanidines and methods of use there of |
US5652269A (en) * | 1991-02-08 | 1997-07-29 | Cambridge Neuroscience, Inc. | Substituted hydrazinecarboximidamides and methods of use thereof |
US5614630A (en) * | 1991-02-08 | 1997-03-25 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US6071969A (en) * | 1991-02-08 | 2000-06-06 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6153604A (en) * | 1993-05-27 | 2000-11-28 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6013675A (en) * | 1993-11-23 | 2000-01-11 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US5955507A (en) * | 1993-11-23 | 1999-09-21 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6156741A (en) * | 1993-11-23 | 2000-12-05 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
US20070265348A1 (en) * | 1994-02-03 | 2007-11-15 | Scion Pharmaceuticals, Inc, A Delaware Corporation | Therapeutic guanidines |
US6288123B1 (en) | 1994-02-03 | 2001-09-11 | Cambridge Neurosciences, Inc. | Therapeutic guanidines |
US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
US6514990B2 (en) | 1996-02-15 | 2003-02-04 | Scion Pharmaceuticals, Inc. | Pharmaceutically active compounds and methods of use |
US6770668B2 (en) | 1996-02-15 | 2004-08-03 | N. Laxma Reddy | Pharmaceutically active compounds and methods of use |
US6358993B1 (en) | 1996-02-15 | 2002-03-19 | Cenes Pharmaceuticals, Inc. | Pharmaceutically active nitrogen ring compounds and methods of use thereof |
US6358696B1 (en) | 1996-07-25 | 2002-03-19 | Mcburney Robert N. | Methods of treatment of eye trauma and disorders |
US6673557B2 (en) | 1996-07-25 | 2004-01-06 | Mcburney Robert N. | Methods of treatment of eye trauma and disorders |
US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
US6756389B2 (en) | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
US7423059B2 (en) | 1996-08-09 | 2008-09-09 | Wyeth | Pharmaceutically active compounds and methods of use |
US6025355A (en) * | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
Also Published As
Publication number | Publication date |
---|---|
DE1214674B (de) | 1966-04-21 |
FR3889M (is) | 1966-01-31 |
GB1110947A (en) | 1968-04-24 |
CH471071A (de) | 1969-04-15 |
SE331090B (is) | 1970-12-14 |
BE656923A (is) | 1965-06-10 |
NL6413937A (is) | 1965-06-14 |
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