IL48792A - N-isoxaolyl-biguanides their preparation and pharmaceutical compositions containing them - Google Patents
N-isoxaolyl-biguanides their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL48792A IL48792A IL48792A IL4879276A IL48792A IL 48792 A IL48792 A IL 48792A IL 48792 A IL48792 A IL 48792A IL 4879276 A IL4879276 A IL 4879276A IL 48792 A IL48792 A IL 48792A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- alkyl radical
- compounds
- therapeutic composition
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229940123208 Biguanide Drugs 0.000 title description 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 5
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 claims description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XQJJUBQZAOMGTK-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine;hydrochloride Chemical compound Cl.CC1=CC(N)=NO1 XQJJUBQZAOMGTK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 1
- SIQWQBQGWREFSE-UHFFFAOYSA-N 1-cyano-2-methylguanidine Chemical compound CNC(N)=NC#N SIQWQBQGWREFSE-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 229940000032 cardiovascular system drug Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1948/75A GB1485315A (en) | 1975-01-16 | 1975-01-16 | Biguanides process for their preparation and applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL48792A0 IL48792A0 (en) | 1976-03-31 |
| IL48792A true IL48792A (en) | 1977-12-30 |
Family
ID=9730864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL48792A IL48792A (en) | 1975-01-16 | 1976-01-05 | N-isoxaolyl-biguanides their preparation and pharmaceutical compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4080460A (instruction) |
| JP (1) | JPS51125280A (instruction) |
| AR (1) | AR208579A1 (instruction) |
| AT (1) | AT347967B (instruction) |
| BE (1) | BE837315A (instruction) |
| CA (1) | CA1058616A (instruction) |
| CH (1) | CH595359A5 (instruction) |
| DE (1) | DE2600474A1 (instruction) |
| DK (1) | DK15976A (instruction) |
| ES (1) | ES444384A1 (instruction) |
| FR (1) | FR2297621A1 (instruction) |
| GB (1) | GB1485315A (instruction) |
| IL (1) | IL48792A (instruction) |
| IT (1) | IT1062179B (instruction) |
| NL (1) | NL7600357A (instruction) |
| SE (1) | SE428377B (instruction) |
| ZA (1) | ZA7657B (instruction) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9884821B2 (en) * | 2013-02-07 | 2018-02-06 | Immunomet Therapeutics Inc. | N1-cyclic amine-N5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1351025A (en) * | 1971-08-20 | 1974-04-24 | Aron Md Samuel J | Oxadiazol-5-yl biguanide derivatives method for their preparation and pharmaceutical compositions containing them |
-
1975
- 1975-01-16 GB GB1948/75A patent/GB1485315A/en not_active Expired
-
1976
- 1976-01-05 CH CH276A patent/CH595359A5/xx not_active IP Right Cessation
- 1976-01-05 BE BE163317A patent/BE837315A/xx not_active IP Right Cessation
- 1976-01-05 FR FR7600054A patent/FR2297621A1/fr active Granted
- 1976-01-05 IL IL48792A patent/IL48792A/en unknown
- 1976-01-06 US US05/646,928 patent/US4080460A/en not_active Expired - Lifetime
- 1976-01-06 ZA ZA00760057A patent/ZA7657B/xx unknown
- 1976-01-08 DE DE19762600474 patent/DE2600474A1/de not_active Withdrawn
- 1976-01-12 AT AT15576A patent/AT347967B/de not_active IP Right Cessation
- 1976-01-13 CA CA243,550A patent/CA1058616A/en not_active Expired
- 1976-01-14 SE SE7600319A patent/SE428377B/xx unknown
- 1976-01-14 NL NL7600357A patent/NL7600357A/xx not_active Application Discontinuation
- 1976-01-15 DK DK15976*#A patent/DK15976A/da unknown
- 1976-01-15 AR AR261931A patent/AR208579A1/es active
- 1976-01-15 IT IT67091/76A patent/IT1062179B/it active
- 1976-01-16 JP JP51003960A patent/JPS51125280A/ja active Pending
- 1976-01-16 ES ES444384A patent/ES444384A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR208579A1 (es) | 1977-02-15 |
| NL7600357A (nl) | 1976-07-20 |
| AU1017676A (en) | 1977-07-14 |
| DK15976A (da) | 1976-07-17 |
| IT1062179B (it) | 1983-07-28 |
| JPS51125280A (en) | 1976-11-01 |
| ZA7657B (en) | 1976-12-29 |
| AT347967B (de) | 1979-01-25 |
| SE428377B (sv) | 1983-06-27 |
| US4080460A (en) | 1978-03-21 |
| GB1485315A (en) | 1977-09-08 |
| ES444384A1 (es) | 1977-05-16 |
| CA1058616A (en) | 1979-07-17 |
| BE837315A (fr) | 1976-07-05 |
| FR2297621B1 (instruction) | 1979-03-23 |
| FR2297621A1 (fr) | 1976-08-13 |
| ATA15576A (de) | 1978-06-15 |
| CH595359A5 (instruction) | 1978-02-15 |
| SE7600319L (sv) | 1976-07-19 |
| DE2600474A1 (de) | 1976-07-22 |
| IL48792A0 (en) | 1976-03-31 |
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