GB1173942A - New 2,3-Dihydro-1,4-Benzoxazines - Google Patents
New 2,3-Dihydro-1,4-BenzoxazinesInfo
- Publication number
- GB1173942A GB1173942A GB25999/67A GB2599967A GB1173942A GB 1173942 A GB1173942 A GB 1173942A GB 25999/67 A GB25999/67 A GB 25999/67A GB 2599967 A GB2599967 A GB 2599967A GB 1173942 A GB1173942 A GB 1173942A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydro
- benzoxazine
- oxo
- alkyl
- carbethoxymethyl
- 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
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical class C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- POGLODLVBYOXAO-UHFFFAOYSA-N 2-(3-oxo-1,4-benzoxazin-4-yl)acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C(=O)COC2=C1 POGLODLVBYOXAO-UHFFFAOYSA-N 0.000 abstract 1
- YGVBQNIVZKEXFO-UHFFFAOYSA-N 2-(3-oxo-1,4-benzoxazin-4-yl)propanoic acid Chemical compound C1=CC=C2N(C(C)C(O)=O)C(=O)COC2=C1 YGVBQNIVZKEXFO-UHFFFAOYSA-N 0.000 abstract 1
- CFZFARSJRUJYDY-UHFFFAOYSA-N 2-(6-chloro-3-oxo-1,4-benzoxazin-4-yl)acetic acid Chemical compound C1=C(Cl)C=C2N(CC(=O)O)C(=O)COC2=C1 CFZFARSJRUJYDY-UHFFFAOYSA-N 0.000 abstract 1
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- PNKJMWWGWBCNQL-UHFFFAOYSA-N ethyl 2-(3-oxo-1,4-benzoxazin-4-yl)acetate Chemical compound C1=CC=C2N(CC(=O)OCC)C(=O)COC2=C1 PNKJMWWGWBCNQL-UHFFFAOYSA-N 0.000 abstract 1
- NZGHBJWHNJXJHE-UHFFFAOYSA-N ethyl 2-(6-chloro-3-oxo-1,4-benzoxazin-4-yl)acetate Chemical compound C1=C(Cl)C=C2N(CC(=O)OCC)C(=O)COC2=C1 NZGHBJWHNJXJHE-UHFFFAOYSA-N 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003387 muscular Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 230000002040 relaxant effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25999/67A GB1173942A (en) | 1967-06-06 | 1967-06-06 | New 2,3-Dihydro-1,4-Benzoxazines |
| FR153267A FR7697M (en:Method) | 1967-06-06 | 1968-05-29 | |
| FR1593525D FR1593525A (en:Method) | 1967-06-06 | 1968-05-29 | |
| BE715883D BE715883A (en:Method) | 1967-06-06 | 1968-05-30 | |
| US734223A US3681330A (en) | 1967-06-06 | 1968-06-04 | 2,3-dihydro-1,4-benzoxazines |
| DK260468AA DK125711B (da) | 1967-06-06 | 1968-06-04 | Analogifremgangsmåde til fremstilling af 3-oxo-2,3-dihydro-1,4-benzoxazinderivater. |
| SE07514/68A SE328889B (en:Method) | 1967-06-06 | 1968-06-05 | |
| CH828268A CH499534A (fr) | 1967-06-06 | 1968-06-05 | Procédé de préparation d'oxo-3a-carboxamidoalcoyl-4 dihydro-2,3 benzoxazines-1,4 |
| NL6807873.A NL158796B (nl) | 1967-06-06 | 1968-06-05 | Werkwijze voor het bereiden van 4-gesubstitueerde-3-oxo-2,3-dihydro-benzo-1,4 oxazinen, werkwijze voor het bereiden van geneesmiddelen met deze verbindingen als actieve stoffen, alsmede aldus verkregen gevormde geneesmiddelen. |
| DE1770565A DE1770565C3 (de) | 1967-06-06 | 1968-06-05 | S-Oxo^-carboxamidomethyl^dihydro-l,4-benzoxazin und pharmazeutische Mittel, enthaltend diese Verbindung |
| US75281A US3705894A (en) | 1967-06-06 | 1970-09-24 | Mycophenolic acid derivatives |
| US269340A US3879522A (en) | 1967-06-06 | 1972-07-06 | New 2,3-dihydro-1,4-benzoxazines in compositions effecting the central nervous system |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25999/67A GB1173942A (en) | 1967-06-06 | 1967-06-06 | New 2,3-Dihydro-1,4-Benzoxazines |
| US73422368A | 1968-06-04 | 1968-06-04 | |
| CH828268A CH499534A (fr) | 1967-06-06 | 1968-06-05 | Procédé de préparation d'oxo-3a-carboxamidoalcoyl-4 dihydro-2,3 benzoxazines-1,4 |
| US7528170A | 1970-09-24 | 1970-09-24 | |
| US269340A US3879522A (en) | 1967-06-06 | 1972-07-06 | New 2,3-dihydro-1,4-benzoxazines in compositions effecting the central nervous system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1173942A true GB1173942A (en) | 1969-12-10 |
Family
ID=27509330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25999/67A Expired GB1173942A (en) | 1967-06-06 | 1967-06-06 | New 2,3-Dihydro-1,4-Benzoxazines |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US3681330A (en:Method) |
| BE (1) | BE715883A (en:Method) |
| CH (1) | CH499534A (en:Method) |
| DE (1) | DE1770565C3 (en:Method) |
| FR (2) | FR1593525A (en:Method) |
| GB (1) | GB1173942A (en:Method) |
| NL (1) | NL158796B (en:Method) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564463A1 (fr) * | 1984-05-18 | 1985-11-22 | Carpibem | Nouveaux derives heterocycliques, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase |
| EP0162776A3 (en) * | 1984-05-18 | 1987-05-06 | Carpibem, Societe Anonyme Dite : | Heterocyclic derivatives, process for their preparation and medicaments useful as aldose reductase inhibitors containing them |
| US4771050A (en) * | 1986-04-17 | 1988-09-13 | Takeda Chemical Industries, Ltd. | Thiolactam-n-acetic acid derivatives |
| EP0290863A3 (en) * | 1987-05-09 | 1989-03-15 | Nihon Tokushu Noyaku Seizo K.K. | Benzoxazine derivative, process and intermediates for its preparation and its use as herbicide |
| EP0441539A3 (en) * | 1990-02-08 | 1992-04-15 | Tanabe Seiyaku Co., Ltd. | Thiazine (or oxazine) derivatives and preparation thereof |
| US5496815A (en) * | 1990-02-08 | 1996-03-05 | Tanabe Seiyaku Co., Ltd. | Thiazine (or oxazine) derivatives and preparation thereof |
| AU774186B2 (en) * | 1999-12-06 | 2004-06-17 | Les Laboratoires Servier | New substituted (dihydro)benzoxazine and (dihydro) benzothiazine compounds, a process for their preparation and pharmaceutical compositions containing them |
| US9101634B2 (en) | 2010-05-20 | 2015-08-11 | Shandong University | Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells |
| GB2568549A (en) * | 2017-11-21 | 2019-05-22 | Univ Leicester | New compounds and uses |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755327A (en) * | 1967-06-05 | 1973-08-28 | Fujisawa Pharmaceutical Co | 1(homo)piperazinyl carbonyl alkyl 2(3h) benzimidozalinones and 2(3h) benzothiozolinone |
| GB1285711A (en) * | 1968-11-08 | 1972-08-16 | Bellon Labor Sa Roger | New benzoxazine derivatives |
| JPS5542995B2 (en:Method) * | 1972-02-24 | 1980-11-04 | ||
| US3868454A (en) * | 1972-08-14 | 1975-02-25 | Lilly Co Eli | Psoriasis treatment with mycophenolic acid derivatives |
| US4333943A (en) * | 1980-04-24 | 1982-06-08 | Miles Laboratories, Inc. | Ethyl 3-(3-indolyl)-3-(5-tetrazolyl) propionate compounds used as anti-hypertensive agents |
| US4686234A (en) * | 1985-11-27 | 1987-08-11 | Syntex (U.S.A) Inc. | Mycophenolic acid derivatives in the treatment of inflammatory diseases, in particular rheumatoid arthritis |
| US4725622A (en) * | 1986-01-23 | 1988-02-16 | Syntex (U.S.A.) Inc. | Mycophenolic acid derivatives in the treatment of rheumatoid arthritis |
| US4753935A (en) * | 1987-01-30 | 1988-06-28 | Syntex (U.S.A.) Inc. | Morpholinoethylesters of mycophenolic acid and pharmaceutical compositions |
| US5177072A (en) * | 1987-01-30 | 1993-01-05 | Syntex (U.S.A.) Inc. | Treatment of autoimmune inflammatory, and psoriatic diseases with heterocyclic aminoalkyl esters of mycophenolic acid and derivatives |
| TW224941B (en:Method) * | 1989-11-08 | 1994-06-11 | Yamanouchi Pharma Co Ltd | |
| US5420126A (en) * | 1989-11-08 | 1995-05-30 | Yamanouchi Pharmaceutical Co., Ltd. | 3,4-dihydro-2H-1,4-benzoxazine derivatives and pharmaceutical compositions containing the same |
| ID18663A (id) * | 1996-04-12 | 1998-04-30 | Novartis Ag | Komposisi farmasi berlapis enterik |
| US6471980B2 (en) | 2000-12-22 | 2002-10-29 | Avantec Vascular Corporation | Intravascular delivery of mycophenolic acid |
| US7077859B2 (en) | 2000-12-22 | 2006-07-18 | Avantec Vascular Corporation | Apparatus and methods for variably controlled substance delivery from implanted prostheses |
| US7083642B2 (en) | 2000-12-22 | 2006-08-01 | Avantec Vascular Corporation | Delivery of therapeutic capable agents |
| EP1667987B1 (en) * | 2003-09-11 | 2008-07-23 | Sandoz AG | Process for the production of mycophenolate mofetil |
| CA2935944A1 (en) * | 2014-01-09 | 2015-07-16 | The J. David Gladstone Institutes, A Testamentary Trust Established Under The Will Of J. David Gladstone | Substituted benzoxazine and related compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2850495A (en) * | 1957-11-12 | 1958-09-02 | Dow Chemical Co | 3, 4-dihydro-2-oxo-2h-1, 4-benzoxazine-4-acetic acids |
| FR1307154A (fr) * | 1960-12-01 | 1962-10-19 | Geigy Ag J R | Antiseptique à base de dérivés de la benzoxazine |
-
1967
- 1967-06-06 GB GB25999/67A patent/GB1173942A/en not_active Expired
-
1968
- 1968-05-29 FR FR1593525D patent/FR1593525A/fr not_active Expired
- 1968-05-29 FR FR153267A patent/FR7697M/fr not_active Expired
- 1968-05-30 BE BE715883D patent/BE715883A/xx unknown
- 1968-06-04 US US734223A patent/US3681330A/en not_active Expired - Lifetime
- 1968-06-05 NL NL6807873.A patent/NL158796B/xx not_active IP Right Cessation
- 1968-06-05 DE DE1770565A patent/DE1770565C3/de not_active Expired
- 1968-06-05 CH CH828268A patent/CH499534A/fr not_active IP Right Cessation
-
1970
- 1970-09-24 US US75281A patent/US3705894A/en not_active Expired - Lifetime
-
1972
- 1972-07-06 US US269340A patent/US3879522A/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564463A1 (fr) * | 1984-05-18 | 1985-11-22 | Carpibem | Nouveaux derives heterocycliques, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase |
| EP0162776A3 (en) * | 1984-05-18 | 1987-05-06 | Carpibem, Societe Anonyme Dite : | Heterocyclic derivatives, process for their preparation and medicaments useful as aldose reductase inhibitors containing them |
| US4755509A (en) * | 1984-05-18 | 1988-07-05 | Carbipem | Heterocyclic aldose reductase inhibitors and methods of using them |
| US4771050A (en) * | 1986-04-17 | 1988-09-13 | Takeda Chemical Industries, Ltd. | Thiolactam-n-acetic acid derivatives |
| EP0290863A3 (en) * | 1987-05-09 | 1989-03-15 | Nihon Tokushu Noyaku Seizo K.K. | Benzoxazine derivative, process and intermediates for its preparation and its use as herbicide |
| EP0441539A3 (en) * | 1990-02-08 | 1992-04-15 | Tanabe Seiyaku Co., Ltd. | Thiazine (or oxazine) derivatives and preparation thereof |
| US5246929A (en) * | 1990-02-08 | 1993-09-21 | Tanabe Seiyaku Co., Ltd. | Naphtho thiazine (or oxaline) derivatives and preparations thereof |
| US5281592A (en) * | 1990-02-08 | 1994-01-25 | Tanabe Seiyaku Co., Ltd. | Thiazine derivatives and preparation thereof |
| US5496815A (en) * | 1990-02-08 | 1996-03-05 | Tanabe Seiyaku Co., Ltd. | Thiazine (or oxazine) derivatives and preparation thereof |
| AU774186B2 (en) * | 1999-12-06 | 2004-06-17 | Les Laboratoires Servier | New substituted (dihydro)benzoxazine and (dihydro) benzothiazine compounds, a process for their preparation and pharmaceutical compositions containing them |
| US9101634B2 (en) | 2010-05-20 | 2015-08-11 | Shandong University | Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells |
| GB2568549A (en) * | 2017-11-21 | 2019-05-22 | Univ Leicester | New compounds and uses |
| WO2019102186A1 (en) * | 2017-11-21 | 2019-05-31 | University Of Leicester | Kynurenine 3-monooxygenase (kmo) inhibitors, and uses and compositions thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL158796B (nl) | 1978-12-15 |
| DE1770565A1 (de) | 1972-03-09 |
| NL6807873A (en:Method) | 1968-12-09 |
| CH499534A (fr) | 1970-11-30 |
| DE1770565C3 (de) | 1979-10-18 |
| FR7697M (en:Method) | 1970-02-23 |
| US3681330A (en) | 1972-08-01 |
| BE715883A (en:Method) | 1968-10-16 |
| DE1770565B2 (de) | 1979-02-22 |
| US3705894A (en) | 1972-12-12 |
| FR1593525A (en:Method) | 1970-06-01 |
| US3879522A (en) | 1975-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |