IE47412B1 - 5-phenyl-2-oxazole carboximidamides and their preparation - Google Patents
5-phenyl-2-oxazole carboximidamides and their preparationInfo
- Publication number
- IE47412B1 IE47412B1 IE2133/78A IE213378A IE47412B1 IE 47412 B1 IE47412 B1 IE 47412B1 IE 2133/78 A IE2133/78 A IE 2133/78A IE 213378 A IE213378 A IE 213378A IE 47412 B1 IE47412 B1 IE 47412B1
- Authority
- IE
- Ireland
- Prior art keywords
- mole
- phenyl
- mixture
- formula
- solid
- Prior art date
Links
- 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 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 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 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- PBFUHGFCLXIQTP-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-oxazole-2-carboximidamide Chemical compound O1C(C(=N)N)=NC=C1C1=CC=C(Cl)C=C1 PBFUHGFCLXIQTP-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 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 16
- 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
- 239000000243 solution Substances 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 150000002923 oximes Chemical class 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
- 150000002825 nitriles Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 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
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000001409 amidines Chemical class 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 229960005333 tetrabenazine Drugs 0.000 description 3
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- -1 phenyl-2-oxazole carboximidamides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VVPKXWNJXPWSTD-UHFFFAOYSA-N 5-phenyl-1,3-oxazole-2-carbonitrile Chemical compound O1C(C#N)=NC=C1C1=CC=CC=C1 VVPKXWNJXPWSTD-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 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 |
|---|---|
| IE782133L IE782133L (en) | 1979-08-27 |
| IE47412B1 true IE47412B1 (en) | 1984-03-07 |
Family
ID=25379300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2133/78A IE47412B1 (en) | 1978-02-27 | 1978-10-27 | 5-phenyl-2-oxazole carboximidamides and their preparation |
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 |
| US4151168A (en) | 1979-04-24 |
| JPS5523827B2 (enExample) | 1980-06-25 |
| GB2014988A (en) | 1979-09-05 |
| SE430063B (sv) | 1983-10-17 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |