GB1563832A - 1,2,4-oxadiazines - Google Patents
1,2,4-oxadiazines Download PDFInfo
- Publication number
- GB1563832A GB1563832A GB16230/78A GB1623078A GB1563832A GB 1563832 A GB1563832 A GB 1563832A GB 16230/78 A GB16230/78 A GB 16230/78A GB 1623078 A GB1623078 A GB 1623078A GB 1563832 A GB1563832 A GB 1563832A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- general formula
- oxo
- methyl
- oxadiazine
- 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
- 150000005065 1,2,4-oxadiazines Chemical class 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- -1 alkylthio radical Chemical class 0.000 claims description 24
- 230000002280 anti-androgenic effect Effects 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- HPYLZSUEFFQHRS-UHFFFAOYSA-N 2h-1,2,4-oxadiazine Chemical compound N1OC=CN=C1 HPYLZSUEFFQHRS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002674 ointment Substances 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 6
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 6
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005843 halogen group Chemical group 0.000 claims description 5
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- 239000006210 lotion Substances 0.000 claims description 3
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- 238000007259 addition reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
- XEZLAJRZQNKEOJ-UHFFFAOYSA-N n-pentylhydroxylamine Chemical compound CCCCCNO XEZLAJRZQNKEOJ-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- VNRCHSPQYNKHIQ-UHFFFAOYSA-N o-(2-bromoethyl)hydroxylamine Chemical compound NOCCBr VNRCHSPQYNKHIQ-UHFFFAOYSA-N 0.000 description 1
- HFMLWSMSMPBTFE-UHFFFAOYSA-N o-(2-bromoethyl)hydroxylamine;hydrobromide Chemical compound Br.NOCCBr HFMLWSMSMPBTFE-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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)
- Cosmetics (AREA)
- Electrodes Of Semiconductors (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7531566A FR2327788A1 (fr) | 1975-10-15 | 1975-10-15 | Medicaments nouveaux derives de la 4-phenyl 5,6-dihydro 1,2,4-oxadiazine 3-one, produits nouveaux derives de la 4-phenyl 5,6-dihydro 1,2,4-oxadiazine 3-one et leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1563832A true GB1563832A (en) | 1980-04-02 |
Family
ID=9161232
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16230/78A Expired GB1563832A (en) | 1975-10-15 | 1976-10-15 | 1,2,4-oxadiazines |
| GB42880/76A Expired GB1563831A (en) | 1975-10-15 | 1976-10-15 | Pharmaceutical compositions containing 1,2,4-oxadiazines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42880/76A Expired GB1563831A (en) | 1975-10-15 | 1976-10-15 | Pharmaceutical compositions containing 1,2,4-oxadiazines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4108993A (enExample) |
| JP (2) | JPS6058727B2 (enExample) |
| BE (1) | BE847290A (enExample) |
| CA (1) | CA1086730A (enExample) |
| CH (1) | CH617685A5 (enExample) |
| DE (1) | DE2646700A1 (enExample) |
| DK (1) | DK150543C (enExample) |
| FR (1) | FR2327788A1 (enExample) |
| GB (2) | GB1563832A (enExample) |
| IE (1) | IE44037B1 (enExample) |
| LU (1) | LU76005A1 (enExample) |
| NL (1) | NL186768C (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2660308B1 (fr) * | 1990-03-30 | 1992-07-17 | Roussel Uclaf | Nouveaux derives soufres du 5,6-dihydro 2-methyl 4-[3-(trifluoromethyl) phenyl] 2h-1,2,4-oxadiazin-3(4h)-one, leur procede de preparation et les intermediaires de ce procede, leur application a titre d'herbicide et les compositions les renfermant. |
| FR2660307B1 (fr) * | 1990-03-30 | 1994-06-03 | Roussel Uclaf | Nouveaux derives du 5,6-dihydro 2-methyl 4-[3-(trifluoromethyl) phenyl] 2h-1,2,4-oxadiazin-3(4h)-one, leur procede de preparation et les intermediaires de ce procede, leur application a titre d'herbicide et les compositions les renfermant. |
| FR2660158A1 (fr) * | 1990-03-30 | 1991-10-04 | Roussel Uclaf | Utilisation comme herbicides de derives de la 5,6-dihydro 2-methyl 4-phenyl 2h-1,2,4-oxadiazin-3(4h)-one, nouveaux derives de celle-ci, leur procede de preparation et les intermediaires de ce procede. |
| US5612377A (en) * | 1994-08-04 | 1997-03-18 | Minnesota Mining And Manufacturing Company | Method of inhibiting leukotriene biosynthesis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238200A (en) * | 1963-06-27 | 1966-03-01 | Olin Mathieson | Oxadiazinediones |
| US3537839A (en) * | 1966-07-02 | 1970-11-03 | Basf Ag | Method for controlling unwanted plant growth with 1,2,4-oxadiazines |
| US3625968A (en) * | 1967-01-12 | 1971-12-07 | Basf Ag | Production of tetrahydro-1,2,4-oxadiazine-3,5-diones |
| FR2039472A5 (enExample) * | 1969-04-03 | 1971-01-15 | Progil | |
| FR2097085A1 (en) * | 1970-07-31 | 1972-03-03 | Pepro | Oxadizing herbicides - for pre - or post-emergence use |
| US3829419A (en) * | 1973-03-26 | 1974-08-13 | Rohm & Haas | Tetrahydro-4h-1,3,5-oxadiazin-4-one |
-
1975
- 1975-10-15 FR FR7531566A patent/FR2327788A1/fr active Granted
-
1976
- 1976-10-05 US US05/729,763 patent/US4108993A/en not_active Expired - Lifetime
- 1976-10-14 BE BE171522A patent/BE847290A/xx not_active IP Right Cessation
- 1976-10-14 JP JP51122355A patent/JPS6058727B2/ja not_active Expired
- 1976-10-14 DK DK462176A patent/DK150543C/da not_active IP Right Cessation
- 1976-10-14 CH CH1303476A patent/CH617685A5/fr not_active IP Right Cessation
- 1976-10-14 LU LU76005A patent/LU76005A1/xx unknown
- 1976-10-15 DE DE19762646700 patent/DE2646700A1/de active Granted
- 1976-10-15 NL NLAANVRAGE7611412,A patent/NL186768C/xx not_active IP Right Cessation
- 1976-10-15 IE IE2283/76A patent/IE44037B1/en not_active IP Right Cessation
- 1976-10-15 CA CA263,490A patent/CA1086730A/fr not_active Expired
- 1976-10-15 GB GB16230/78A patent/GB1563832A/en not_active Expired
- 1976-10-15 GB GB42880/76A patent/GB1563831A/en not_active Expired
-
1985
- 1985-07-02 JP JP60144084A patent/JPS6156173A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE44037L (en) | 1977-04-15 |
| GB1563831A (en) | 1980-04-02 |
| JPS6058727B2 (ja) | 1985-12-21 |
| DE2646700C2 (enExample) | 1987-11-19 |
| JPS6156173A (ja) | 1986-03-20 |
| DE2646700A1 (de) | 1977-04-21 |
| FR2327788A1 (fr) | 1977-05-13 |
| LU76005A1 (enExample) | 1977-05-25 |
| BE847290A (fr) | 1977-04-14 |
| NL186768B (nl) | 1990-09-17 |
| CA1086730A (fr) | 1980-09-30 |
| JPS6319513B2 (enExample) | 1988-04-22 |
| NL186768C (nl) | 1991-02-18 |
| NL7611412A (nl) | 1977-04-19 |
| DK150543C (da) | 1987-09-28 |
| FR2327788B1 (enExample) | 1979-10-12 |
| US4108993A (en) | 1978-08-22 |
| CH617685A5 (enExample) | 1980-06-13 |
| JPS5251380A (en) | 1977-04-25 |
| DK150543B (da) | 1987-03-23 |
| IE44037B1 (en) | 1981-07-29 |
| DK462176A (da) | 1977-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921015 |