SE430063B - 5-fenyl-2-oxazolkarboximidamider - Google Patents
5-fenyl-2-oxazolkarboximidamiderInfo
- Publication number
- SE430063B SE430063B SE7811577A SE7811577A SE430063B SE 430063 B SE430063 B SE 430063B SE 7811577 A SE7811577 A SE 7811577A SE 7811577 A SE7811577 A SE 7811577A SE 430063 B SE430063 B SE 430063B
- Authority
- SE
- Sweden
- Prior art keywords
- mol
- solid
- mixture
- hours
- give
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 6
- RZDUJCWHBLKKAX-UHFFFAOYSA-N 5-phenyl-1,3-oxazole-2-carboximidamide Chemical class O1C(C(=N)N)=NC=C1C1=CC=CC=C1 RZDUJCWHBLKKAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- YLFXMAPOCKKEOS-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-oxazole-2-carboximidamide;hydrochloride Chemical group Cl.O1C(C(=N)N)=NC=C1C1=CC=C(Cl)C=C1 YLFXMAPOCKKEOS-UHFFFAOYSA-N 0.000 claims 1
- DESDKOKDDKOPDW-UHFFFAOYSA-N 5-(4-nitrophenyl)-1,3-oxazole-2-carboximidamide;hydrochloride Chemical compound Cl.O1C(C(=N)N)=NC=C1C1=CC=C([N+]([O-])=O)C=C1 DESDKOKDDKOPDW-UHFFFAOYSA-N 0.000 claims 1
- AFZOHAAQYMBMPW-UHFFFAOYSA-N 5-phenyl-1,3-oxazole-2-carboximidamide;hydrochloride Chemical group Cl.O1C(C(=N)N)=NC=C1C1=CC=CC=C1 AFZOHAAQYMBMPW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- -1 amino Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XOBBBHIMJATSML-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-oxazole-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=CN=C(C#N)O1 XOBBBHIMJATSML-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PMMPVJFLNYXNTB-UHFFFAOYSA-N N-[(5-phenyl-1,3-oxazol-2-yl)methylidene]hydroxylamine Chemical compound O1C(C=NO)=NC=C1C1=CC=CC=C1 PMMPVJFLNYXNTB-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (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 |
|---|---|---|---|
| US05/881,827 US4151168A (en) | 1978-02-27 | 1978-02-27 | 5-Phenyl-2-oxazole carboximidamides as antidepressants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7811577L SE7811577L (sv) | 1979-08-28 |
| SE430063B true SE430063B (sv) | 1983-10-17 |
Family
ID=25379300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7811577A SE430063B (sv) | 1978-02-27 | 1978-11-09 | 5-fenyl-2-oxazolkarboximidamider |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4151168A (enExample) |
| JP (1) | JPS54115371A (enExample) |
| AU (1) | AU518273B2 (enExample) |
| BE (1) | BE873853A (enExample) |
| CA (1) | CA1106385A (enExample) |
| CH (1) | CH638505A5 (enExample) |
| DE (1) | DE2907199A1 (enExample) |
| ES (1) | ES477715A1 (enExample) |
| FR (1) | FR2418229A1 (enExample) |
| GB (1) | GB2014988B (enExample) |
| IE (1) | IE47412B1 (enExample) |
| IT (1) | IT1115788B (enExample) |
| MX (1) | MX5082E (enExample) |
| NL (1) | NL190774C (enExample) |
| SE (1) | SE430063B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59135008U (ja) * | 1983-02-28 | 1984-09-10 | 松下電工株式会社 | 分電盤装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL135043C (enExample) * | 1963-10-11 | |||
| GB1075259A (en) * | 1964-12-18 | 1967-07-12 | Monsanto Chem Australia Ltd | Novel substituted benzimidazoles and use therefor |
| FR1537684A (fr) * | 1965-12-29 | 1968-09-07 | Monsanto Chem Australia Ltd | Procédé de préparation des 2-azolin-2-yl-benzimidazoles |
-
1978
- 1978-02-27 US US05/881,827 patent/US4151168A/en not_active Expired - Lifetime
- 1978-10-25 CA CA314,176A patent/CA1106385A/en not_active Expired
- 1978-10-27 IE IE2133/78A patent/IE47412B1/en not_active IP Right Cessation
- 1978-11-01 AU AU41232/78A patent/AU518273B2/en not_active Expired
- 1978-11-09 SE SE7811577A patent/SE430063B/sv not_active IP Right Cessation
- 1978-11-13 GB GB7844256A patent/GB2014988B/en not_active Expired
- 1978-11-20 JP JP14325978A patent/JPS54115371A/ja active Granted
- 1978-11-24 MX MX787556U patent/MX5082E/es unknown
-
1979
- 1979-01-11 NL NL7900239A patent/NL190774C/xx not_active IP Right Cessation
- 1979-01-31 BE BE0/193200A patent/BE873853A/xx not_active IP Right Cessation
- 1979-02-01 IT IT47857/79A patent/IT1115788B/it active
- 1979-02-14 ES ES477715A patent/ES477715A1/es not_active Expired
- 1979-02-20 CH CH163979A patent/CH638505A5/de not_active IP Right Cessation
- 1979-02-23 FR FR7904741A patent/FR2418229A1/fr active Granted
- 1979-02-23 DE DE19792907199 patent/DE2907199A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU518273B2 (en) | 1981-09-24 |
| FR2418229B1 (enExample) | 1983-03-18 |
| GB2014988B (en) | 1982-06-09 |
| NL190774C (nl) | 1994-08-16 |
| AU4123278A (en) | 1979-09-06 |
| DE2907199C2 (enExample) | 1988-03-24 |
| IE47412B1 (en) | 1984-03-07 |
| US4151168A (en) | 1979-04-24 |
| JPS5523827B2 (enExample) | 1980-06-25 |
| GB2014988A (en) | 1979-09-05 |
| SE7811577L (sv) | 1979-08-28 |
| JPS54115371A (en) | 1979-09-07 |
| IT1115788B (it) | 1986-02-03 |
| ES477715A1 (es) | 1980-04-01 |
| MX5082E (es) | 1983-03-14 |
| DE2907199A1 (de) | 1979-08-30 |
| FR2418229A1 (fr) | 1979-09-21 |
| NL7900239A (nl) | 1979-08-29 |
| IE782133L (en) | 1979-08-27 |
| IT7947857A0 (it) | 1979-02-01 |
| NL190774B (nl) | 1994-03-16 |
| BE873853A (fr) | 1979-07-31 |
| CH638505A5 (de) | 1983-09-30 |
| CA1106385A (en) | 1981-08-04 |
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| Date | Code | Title | Description |
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| NAL | Patent in force |
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