NO121045B - - Google Patents
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- Publication number
- NO121045B NO121045B NO169099A NO16909967A NO121045B NO 121045 B NO121045 B NO 121045B NO 169099 A NO169099 A NO 169099A NO 16909967 A NO16909967 A NO 16909967A NO 121045 B NO121045 B NO 121045B
- Authority
- NO
- Norway
- Prior art keywords
- benzoxazin
- carbon atoms
- alkyl group
- alkyl
- mean hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- -1 dimethyl-3,1-benzoxazin-2-one Chemical compound 0.000 description 5
- 239000007858 starting material Substances 0.000 description 4
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
- GTYZDORKFFSTLS-UHFFFAOYSA-N 2h-3,1-benzoxazine Chemical compound C1=CC=CC2=NCOC=C21 GTYZDORKFFSTLS-UHFFFAOYSA-N 0.000 description 1
- GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical class C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000001670 myorelaxant effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000003699 striated muscle Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
-
- 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
- C07D265/20—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 4
- C07D265/22—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2105166 | 1966-08-03 | ||
| IT1800566 | 1966-08-03 | ||
| IT1516667 | 1967-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121045B true NO121045B (da) | 1971-01-11 |
Family
ID=27272868
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169228A NO121275B (da) | 1966-08-03 | 1967-08-01 | |
| NO169099A NO121045B (da) | 1966-08-03 | 1967-09-29 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169228A NO121275B (da) | 1966-08-03 | 1967-08-01 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3526621A (da) |
| BE (2) | BE702201A (da) |
| CH (1) | CH478828A (da) |
| DE (2) | DE1695756C3 (da) |
| DK (2) | DK118877B (da) |
| ES (2) | ES343737A1 (da) |
| FR (2) | FR6494M (da) |
| GB (1) | GB1135899A (da) |
| IL (1) | IL28427A (da) |
| NL (2) | NL6710332A (da) |
| NO (2) | NO121275B (da) |
| SE (2) | SE331997B (da) |
| YU (2) | YU31634B (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4301283A (en) * | 1979-09-27 | 1981-11-17 | Sterling Drug Inc. | Process for preparing 2-oxo-dihydrobenzo(d)(1,3)-oxazines |
| DE3026534A1 (de) * | 1980-07-12 | 1982-03-18 | C.H. Boehringer Sohn, 6507 Ingelheim | 3,1-benzoxazin-2-one, ihre herstellung und verwendung |
| DE3217012A1 (de) * | 1982-05-06 | 1983-11-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Benzoxazin-2-one, deren herstellung und diese verbindungen enthaltende arzneimittel |
| IL106507A (en) * | 1992-08-07 | 1997-11-20 | Merck & Co Inc | Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type |
| US5519021A (en) * | 1992-08-07 | 1996-05-21 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
| AU1694295A (en) * | 1994-01-28 | 1995-08-15 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
| EP0929533B1 (en) * | 1996-10-02 | 2003-09-03 | Bristol-Myers Squibb Pharma Company | 4,4-disubstituted-1,4-dihydro-2h-3,1-benzoxazin-2-ones useful as hiv reverse transcriptase inhibitors and intermediates and processes for making the same |
| US5874430A (en) * | 1996-10-02 | 1999-02-23 | Dupont Pharmaceuticals Company | 4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same |
| US5932726A (en) * | 1996-12-16 | 1999-08-03 | Dupont Pharmaceuticals Company | Asymmetric synthesis of benzoxazinones |
| US6509334B1 (en) * | 1999-05-04 | 2003-01-21 | American Home Products Corporation | Cyclocarbamate derivatives as progesterone receptor modulators |
| US6358948B1 (en) | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| UA73119C2 (en) * | 2000-04-19 | 2005-06-15 | American Home Products Corpoir | Derivatives of cyclic thiocarbamates, pharmaceutical composition including noted derivatives of cyclic thiocarbamates and active ingredients of medicines as modulators of progesterone receptors |
| AU2005237520B2 (en) | 2004-04-27 | 2012-01-19 | Wyeth | Purification of progesterone receptor modulators |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047573A (en) * | 1962-07-31 | N-alkylamido substituted | ||
| US2940971A (en) * | 1960-06-14 | Tetrahydrooxazenones | ||
| US1951807A (en) * | 1931-04-17 | 1934-03-20 | Holimann La Roche Inc | 4-phenalkyl-3-keto-3.4-dihydro-1.4-benzoxazines and process for the manufacture of same |
| US2947745A (en) * | 1958-08-11 | 1960-08-02 | Smith Kline French Lab | Substituted phenoxazine sedative agents |
| US3280120A (en) * | 1964-03-09 | 1966-10-18 | Rexall Drug Chemical | Substituted benzoxazines, process therefor and intermediates |
-
1967
- 1967-07-25 US US655749A patent/US3526621A/en not_active Expired - Lifetime
- 1967-07-26 NL NL6710332A patent/NL6710332A/xx unknown
- 1967-07-29 DE DE1695756A patent/DE1695756C3/de not_active Expired
- 1967-07-31 GB GB35019/67A patent/GB1135899A/en not_active Expired
- 1967-07-31 IL IL28427A patent/IL28427A/en unknown
- 1967-08-01 NO NO169228A patent/NO121275B/no unknown
- 1967-08-01 FR FR116413A patent/FR6494M/fr not_active Expired
- 1967-08-01 YU YU1526/67A patent/YU31634B/xx unknown
- 1967-08-02 CH CH1088467A patent/CH478828A/de not_active IP Right Cessation
- 1967-08-02 SE SE11055/67A patent/SE331997B/xx unknown
- 1967-08-02 DK DK394667AA patent/DK118877B/da unknown
- 1967-08-02 BE BE702201D patent/BE702201A/xx not_active Expired
- 1967-08-02 ES ES343737A patent/ES343737A1/es not_active Expired
- 1967-09-25 NL NL6713047A patent/NL6713047A/xx unknown
- 1967-09-28 DE DE1695780A patent/DE1695780C3/de not_active Expired
- 1967-09-28 FR FR122591A patent/FR93909E/fr not_active Expired
- 1967-09-28 YU YU1900/67A patent/YU31636B/xx unknown
- 1967-09-29 DK DK485367AA patent/DK111568B/da unknown
- 1967-09-29 NO NO169099A patent/NO121045B/no unknown
- 1967-09-29 SE SE13396/67A patent/SE337823B/xx unknown
- 1967-09-30 ES ES345647A patent/ES345647A2/es not_active Expired
- 1967-10-02 BE BE704583D patent/BE704583A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES343737A1 (es) | 1968-10-16 |
| NL6713047A (da) | 1968-10-21 |
| YU152667A (en) | 1973-02-28 |
| CH478828A (de) | 1969-09-30 |
| ES345647A2 (es) | 1968-11-16 |
| DE1695780A1 (de) | 1971-04-29 |
| FR6494M (da) | 1968-11-25 |
| DK111568B (da) | 1968-09-16 |
| NO121275B (da) | 1971-02-08 |
| DE1695756C3 (de) | 1978-10-05 |
| YU190067A (en) | 1973-02-28 |
| US3526621A (en) | 1970-09-01 |
| SE337823B (da) | 1971-08-23 |
| IL28427A (en) | 1971-04-28 |
| SE331997B (da) | 1971-01-25 |
| BE704583A (da) | 1968-04-02 |
| FR93909E (fr) | 1969-06-06 |
| NL6710332A (da) | 1968-02-05 |
| BE702201A (da) | 1968-02-02 |
| DE1695756A1 (de) | 1972-03-02 |
| DE1695756B2 (de) | 1978-02-09 |
| YU31634B (en) | 1973-10-31 |
| YU31636B (en) | 1973-10-31 |
| GB1135899A (en) | 1968-12-04 |
| DE1695780B2 (de) | 1978-12-21 |
| DE1695780C3 (de) | 1979-08-23 |
| DK118877B (da) | 1970-10-19 |
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