NL8006595A - Oxazolinederivaten, werkwijzen ter bereiding ervan alsmede farmaceutische preparaten. - Google Patents
Oxazolinederivaten, werkwijzen ter bereiding ervan alsmede farmaceutische preparaten. Download PDFInfo
- Publication number
- NL8006595A NL8006595A NL8006595A NL8006595A NL8006595A NL 8006595 A NL8006595 A NL 8006595A NL 8006595 A NL8006595 A NL 8006595A NL 8006595 A NL8006595 A NL 8006595A NL 8006595 A NL8006595 A NL 8006595A
- Authority
- NL
- Netherlands
- Prior art keywords
- phenyl
- formula
- dimethyl
- oxazoline
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title description 7
- 150000002918 oxazolines Chemical class 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000003178 anti-diabetic effect Effects 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
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- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- FRGAJCJAEQEGQB-UHFFFAOYSA-N 2,2-dimethyl-3-phenylazirine Chemical compound CC1(C)N=C1C1=CC=CC=C1 FRGAJCJAEQEGQB-UHFFFAOYSA-N 0.000 description 4
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- 241000700159 Rattus Species 0.000 description 4
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1141079 | 1979-12-21 | ||
| CH1141079 | 1979-12-21 | ||
| CH785680 | 1980-10-21 | ||
| CH785680 | 1980-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8006595A true NL8006595A (nl) | 1981-07-16 |
Family
ID=25702346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006595A NL8006595A (nl) | 1979-12-21 | 1980-12-03 | Oxazolinederivaten, werkwijzen ter bereiding ervan alsmede farmaceutische preparaten. |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4317914A (cs) |
| EP (1) | EP0031562B1 (cs) |
| KR (2) | KR840002303B1 (cs) |
| AR (1) | AR230052A1 (cs) |
| AU (1) | AU540643B2 (cs) |
| BR (1) | BR8008189A (cs) |
| CA (1) | CA1169074A (cs) |
| CS (1) | CS221960B2 (cs) |
| CU (1) | CU21295A3 (cs) |
| DE (2) | DE3067063D1 (cs) |
| DK (1) | DK149771B (cs) |
| ES (1) | ES8203355A1 (cs) |
| FI (1) | FI69452C (cs) |
| FR (1) | FR2471978A1 (cs) |
| GB (1) | GB2066250B (cs) |
| GR (1) | GR72809B (cs) |
| HU (1) | HU182258B (cs) |
| IE (1) | IE51008B1 (cs) |
| IL (1) | IL61713A (cs) |
| IT (1) | IT1134431B (cs) |
| LU (1) | LU83017A1 (cs) |
| MC (1) | MC1366A1 (cs) |
| MY (1) | MY8500271A (cs) |
| NL (1) | NL8006595A (cs) |
| NO (1) | NO154011C (cs) |
| NZ (1) | NZ195830A (cs) |
| PT (1) | PT72249B (cs) |
| SE (1) | SE8009015L (cs) |
| ZW (1) | ZW28780A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952360A (en) * | 1997-08-28 | 1999-09-14 | Eli Lilly And Company | Method for treating neuropathic pain |
| US5942530A (en) * | 1997-08-28 | 1999-08-24 | Eli Lilly And Company | Method for treating pain |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
-
1980
- 1980-11-17 CA CA000364793A patent/CA1169074A/en not_active Expired
- 1980-11-19 CS CS807848A patent/CS221960B2/cs unknown
- 1980-11-24 IT IT26191/80A patent/IT1134431B/it active
- 1980-11-26 ZW ZW287/80A patent/ZW28780A1/xx unknown
- 1980-12-03 NL NL8006595A patent/NL8006595A/nl not_active Application Discontinuation
- 1980-12-12 US US06/215,965 patent/US4317914A/en not_active Expired - Fee Related
- 1980-12-15 BR BR8008189A patent/BR8008189A/pt unknown
- 1980-12-15 HU HU802991A patent/HU182258B/hu unknown
- 1980-12-15 NZ NZ195830A patent/NZ195830A/en unknown
- 1980-12-15 IL IL61713A patent/IL61713A/xx unknown
- 1980-12-16 AU AU65420/80A patent/AU540643B2/en not_active Ceased
- 1980-12-17 FI FI803940A patent/FI69452C/fi not_active IP Right Cessation
- 1980-12-18 FR FR8026922A patent/FR2471978A1/fr active Granted
- 1980-12-18 MC MC801490A patent/MC1366A1/xx unknown
- 1980-12-19 NO NO803890A patent/NO154011C/no unknown
- 1980-12-19 CU CU8035394A patent/CU21295A3/es unknown
- 1980-12-19 SE SE8009015A patent/SE8009015L/xx not_active Application Discontinuation
- 1980-12-19 DK DK545980AA patent/DK149771B/da not_active Application Discontinuation
- 1980-12-19 LU LU83017A patent/LU83017A1/de unknown
- 1980-12-19 PT PT72249A patent/PT72249B/pt unknown
- 1980-12-19 AR AR283734A patent/AR230052A1/es active
- 1980-12-19 GB GB8040801A patent/GB2066250B/en not_active Expired
- 1980-12-19 DE DE8080108065T patent/DE3067063D1/de not_active Expired
- 1980-12-19 IE IE2682/80A patent/IE51008B1/en unknown
- 1980-12-19 DE DE19803048169 patent/DE3048169A1/de not_active Withdrawn
- 1980-12-19 EP EP80108065A patent/EP0031562B1/de not_active Expired
- 1980-12-20 KR KR1019800004867A patent/KR840002303B1/ko not_active Expired
- 1980-12-20 ES ES498028A patent/ES8203355A1/es not_active Expired
- 1980-12-20 GR GR63731A patent/GR72809B/el unknown
-
1981
- 1981-11-12 US US06/320,262 patent/US4360530A/en not_active Expired - Fee Related
-
1984
- 1984-10-05 KR KR1019840006157A patent/KR850000210B1/ko not_active Expired
-
1985
- 1985-12-30 MY MY271/85A patent/MY8500271A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |