GB1110947A - Guanidines - Google Patents
GuanidinesInfo
- Publication number
- GB1110947A GB1110947A GB49408/63A GB4940863A GB1110947A GB 1110947 A GB1110947 A GB 1110947A GB 49408/63 A GB49408/63 A GB 49408/63A GB 4940863 A GB4940863 A GB 4940863A GB 1110947 A GB1110947 A GB 1110947A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- amine
- reacting
- compound
- followed
- 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
- 150000002357 guanidines Chemical class 0.000 title 1
- 150000001412 amines Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 abstract 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- -1 cyanogen halide Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 238000002664 inhalation therapy Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
Classifications
-
- 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)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Compounds of the formula <FORM:1110947/C2/1> wherein R is C5- 7 cycloalkyl opt. substd., R1 is H or C1- 4 alkyl, R2 is C1- 4 alkyl, and R3, R4 and R5 are the same or different, are H or C1- 4 alkyl are prepared by reacting an amine of the formula R-NH-C.R1R2-CH2NHR6 where R6 is H either with a thiourea derivative <FORM:1110947/C2/2> where R7 is an alkyl or aralkyl group, or a cyanamide or N-nitro guanidine or an N-alkyl-N-nitroso guanidine or with cyanogen halide followed by reaction of the product with NH3 or an amine or with a compound <FORM:1110947/C2/3> where R8 is alkoxy or aralkoxy or a group <FORM:1110947/C2/4> or a salt thereof or where R6 is CSNH2 with HgO and NH3 or an amine and where R3 R4 or R5 is alkyl reacting the compound where R3, R4 or R5 is H with an alkylating agent. In the process the amine (II) where R6 is H is prepared either by reduction of the corresponding nitrile R-NH-C-R1R2-CN n turn prepared by reacting a compound R1COR2 with an amine RNH2 followed by reaction of the product with a cyanide or by reacting an amine RNH2 with a cyanhydrin of R1COR2, or by condensation of a C5- 7-cycloalkanone with a diamine H2N-CR1R2-CH2-NH2 followed by reduction of the Schipp base. Pharmaceutical compositions comprise the compounds (I) and a carrier therefor. The compositions, which show hypotensive activity, may be in a form suitable for aral, rectal or parenteral administration or inhalation therapy.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49408/63A GB1110947A (en) | 1963-12-13 | 1963-12-13 | Guanidines |
| DEE27090A DE1214674B (en) | 1963-12-13 | 1964-05-22 | Process for the production of guanidine derivatives |
| US413315A US3409669A (en) | 1963-12-13 | 1964-11-23 | 2-(cyclohexylamino)-2-methyl-propylguanidine-1 and the salts and hydrate thereof |
| CH1540864A CH471071A (en) | 1963-12-13 | 1964-11-30 | Process for the preparation of guanidine compounds |
| NL6413937A NL6413937A (en) | 1963-12-13 | 1964-12-01 | |
| FR997779A FR3889M (en) | 1963-12-13 | 1964-12-08 | |
| FR997785A FR1430921A (en) | 1963-12-13 | 1964-12-08 | New guanidine derivatives and their preparation process |
| BE656923D BE656923A (en) | 1963-12-13 | 1964-12-10 | |
| SE14996/64A SE331090B (en) | 1963-12-13 | 1964-12-11 |
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 |
|---|---|
| GB1110947A true GB1110947A (en) | 1968-04-24 |
Family
ID=10452240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49408/63A Expired GB1110947A (en) | 1963-12-13 | 1963-12-13 | Guanidines |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3409669A (en) |
| BE (1) | BE656923A (en) |
| CH (1) | CH471071A (en) |
| DE (1) | DE1214674B (en) |
| FR (1) | FR3889M (en) |
| GB (1) | GB1110947A (en) |
| NL (1) | NL6413937A (en) |
| SE (1) | SE331090B (en) |
Families Citing this family (18)
| 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 |
| 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 |
| PT96930B (en) | 1990-03-02 | 1998-06-30 | Univ Oregon | METHOD FOR THE USE OF TRI-TETRA-SUBSTITUTED GUANIDINES AS ANTAGONISTS OF AMINO ACID DRIVERS |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| JPH05508836A (en) * | 1990-05-25 | 1993-12-09 | オレゴン州 | Substituted guanidines with high binding to sigma receptors and their uses |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| 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 |
| IE20030530A1 (en) * | 1991-02-08 | 2003-10-01 | Cambridge Neuroscience Inc | Guanidines and derivatives |
| WO1994027591A1 (en) * | 1993-05-27 | 1994-12-08 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| EP0739200A4 (en) * | 1993-11-23 | 1997-12-17 | Cambridge Neuroscience Inc | Therapeutic substituted guanidines |
| JPH09509156A (en) * | 1994-02-03 | 1997-09-16 | ケンブリッジ・ニューロサイエンス・インコーポレーテッド | Therapeutic guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| 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 |
Family Cites Families (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/en active Pending
- 1964-11-23 US US413315A patent/US3409669A/en not_active Expired - Lifetime
- 1964-11-30 CH CH1540864A patent/CH471071A/en 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
Also Published As
| Publication number | Publication date |
|---|---|
| US3409669A (en) | 1968-11-05 |
| DE1214674B (en) | 1966-04-21 |
| BE656923A (en) | 1965-06-10 |
| FR3889M (en) | 1966-01-31 |
| SE331090B (en) | 1970-12-14 |
| CH471071A (en) | 1969-04-15 |
| NL6413937A (en) | 1965-06-14 |
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