NO794289L - Fremgangsmaate ved fremstilling av 7-klor-2-methyl-3,3a-dihydro-2h,9h-isoxazolo-(3,2-b)-(1,3)-benzoxazin-9-on - Google Patents
Fremgangsmaate ved fremstilling av 7-klor-2-methyl-3,3a-dihydro-2h,9h-isoxazolo-(3,2-b)-(1,3)-benzoxazin-9-onInfo
- Publication number
- NO794289L NO794289L NO794289A NO794289A NO794289L NO 794289 L NO794289 L NO 794289L NO 794289 A NO794289 A NO 794289A NO 794289 A NO794289 A NO 794289A NO 794289 L NO794289 L NO 794289L
- Authority
- NO
- Norway
- Prior art keywords
- approx
- dihydro
- methyl
- chloro
- benzoxazin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- OJGJQQNLRVNIKE-UHFFFAOYSA-N meseclazone Chemical compound O1C2=CC=C(Cl)C=C2C(=O)N2C1CC(C)O2 OJGJQQNLRVNIKE-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 7
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- VGDCRPRQQPVICX-UHFFFAOYSA-N 5-chloro-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=CC=C1O VGDCRPRQQPVICX-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 4
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 229940116269 uric acid Drugs 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 2
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- NKBASRXWGAGQDP-UHFFFAOYSA-M 5-chlorosalicylate Chemical compound OC1=CC=C(Cl)C=C1C([O-])=O NKBASRXWGAGQDP-UHFFFAOYSA-M 0.000 description 1
- -1 6-chloro-2-(2-chloropropyl)-2,3-dihydro-3-hydroxy-4H-1,3-benzoxazine -5-on Chemical compound 0.000 description 1
- GIQSMIHDVLQLKN-UHFFFAOYSA-N 6-chloro-2-methyl-3,3a-dihydro-2h-[1,2]oxazolo[3,2-b][1,3]benzoxazin-9-one Chemical compound O1C2=CC(Cl)=CC=C2C(=O)N2C1CC(C)O2 GIQSMIHDVLQLKN-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
- 206010030113 Oedema Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000003424 uricosuric effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/000,142 US4224443A (en) | 1978-12-29 | 1978-12-29 | Chemical process for preparation of 7-chloro-2-methyl-3,3a-dihydro-2H,9H-isoxazolo(3,2-b)(1,3)-benzoxazin-9-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO794289L true NO794289L (no) | 1980-07-01 |
Family
ID=21690115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO794289A NO794289L (no) | 1978-12-29 | 1979-12-27 | Fremgangsmaate ved fremstilling av 7-klor-2-methyl-3,3a-dihydro-2h,9h-isoxazolo-(3,2-b)-(1,3)-benzoxazin-9-on |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4224443A (pt) |
| JP (1) | JPS55115884A (pt) |
| AT (1) | ATA817779A (pt) |
| AU (1) | AU539107B2 (pt) |
| BE (1) | BE880957A (pt) |
| BR (1) | BR7908511A (pt) |
| CA (1) | CA1138866A (pt) |
| CH (1) | CH645115A5 (pt) |
| DE (1) | DE2952385A1 (pt) |
| DK (1) | DK549979A (pt) |
| FI (1) | FI793863A (pt) |
| FR (1) | FR2445335A1 (pt) |
| GB (1) | GB2039904B (pt) |
| LU (1) | LU82049A1 (pt) |
| MX (1) | MX5916E (pt) |
| NL (1) | NL7909262A (pt) |
| NO (1) | NO794289L (pt) |
| SE (1) | SE7910111L (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5988909A (en) * | 1991-12-02 | 1999-11-23 | Luke, Jr.; Stanley C. | Writing instrument with ergonomic grip |
| US6164855A (en) * | 1998-03-26 | 2000-12-26 | Bic Corporation | Writing instrument with finger gripping device |
| US6062753A (en) * | 1998-08-17 | 2000-05-16 | Pentech International Inc. | Writing instrument with enhanced tactile control and gripping comfort and method of making same |
| GB2583775B (en) * | 2019-05-10 | 2023-10-18 | Aerofoil Energy Ltd | Improvements to refrigerators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3684805A (en) * | 1969-03-24 | 1972-08-15 | Carter Wallace | 2,3,4,4a-TETRAHYDRO-10H-1,2-OXAZINO {8 3,2-b{9 (1,3)BENZOXAZIN-10-ONES |
| US3598814A (en) * | 1970-01-21 | 1971-08-10 | Carter Wallace | 3,3a-dihydro-2h,9h-isoxazolo(3,2-b)(1,3) benzoxazin-9-ones |
| US3903083A (en) * | 1973-11-19 | 1975-09-02 | Merck & Co Inc | 3,3A-Dihydro-2H,9H-isoxazolo(3,2-b)(1,3)benzoxazin-9-ones |
-
1978
- 1978-12-29 US US06/000,142 patent/US4224443A/en not_active Expired - Lifetime
-
1979
- 1979-12-07 SE SE7910111A patent/SE7910111L/xx not_active Application Discontinuation
- 1979-12-11 FI FI793863A patent/FI793863A/fi not_active Application Discontinuation
- 1979-12-14 CA CA000342002A patent/CA1138866A/en not_active Expired
- 1979-12-21 JP JP16571579A patent/JPS55115884A/ja active Pending
- 1979-12-21 DK DK549979A patent/DK549979A/da not_active Application Discontinuation
- 1979-12-21 NL NL7909262A patent/NL7909262A/nl not_active Application Discontinuation
- 1979-12-24 DE DE19792952385 patent/DE2952385A1/de not_active Withdrawn
- 1979-12-26 BR BR7908511A patent/BR7908511A/pt unknown
- 1979-12-27 FR FR7931822A patent/FR2445335A1/fr active Granted
- 1979-12-27 NO NO794289A patent/NO794289L/no unknown
- 1979-12-28 CH CH1150779A patent/CH645115A5/fr not_active IP Right Cessation
- 1979-12-28 AT AT0817779A patent/ATA817779A/de not_active Application Discontinuation
- 1979-12-28 BE BE0/198821A patent/BE880957A/fr not_active IP Right Cessation
- 1979-12-28 AU AU54235/79A patent/AU539107B2/en not_active Ceased
- 1979-12-28 LU LU82049A patent/LU82049A1/xx unknown
- 1979-12-31 GB GB7944635A patent/GB2039904B/en not_active Expired
-
1980
- 1980-01-02 MX MX808572U patent/MX5916E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2445335A1 (fr) | 1980-07-25 |
| DE2952385A1 (de) | 1980-07-10 |
| BE880957A (fr) | 1980-06-30 |
| GB2039904B (en) | 1983-05-11 |
| GB2039904A (en) | 1980-08-20 |
| US4224443A (en) | 1980-09-23 |
| NL7909262A (nl) | 1980-07-01 |
| LU82049A1 (fr) | 1981-07-23 |
| JPS55115884A (en) | 1980-09-06 |
| AU539107B2 (en) | 1984-09-13 |
| CH645115A5 (fr) | 1984-09-14 |
| BR7908511A (pt) | 1980-09-23 |
| MX5916E (es) | 1984-08-24 |
| DK549979A (da) | 1980-06-30 |
| CA1138866A (en) | 1983-01-04 |
| AU5423579A (en) | 1980-07-03 |
| FI793863A (fi) | 1980-06-30 |
| ATA817779A (de) | 1984-04-15 |
| FR2445335B1 (pt) | 1984-12-07 |
| SE7910111L (sv) | 1980-06-30 |
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