IL25858A - 3,1-benzothiazines and 3,1-benzoxazines,process for preparing them and compositions thereof - Google Patents
3,1-benzothiazines and 3,1-benzoxazines,process for preparing them and compositions thereofInfo
- Publication number
- IL25858A IL25858A IL25858A IL2585866A IL25858A IL 25858 A IL25858 A IL 25858A IL 25858 A IL25858 A IL 25858A IL 2585866 A IL2585866 A IL 2585866A IL 25858 A IL25858 A IL 25858A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- chloro
- benzothiazine
- grams
- amino
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 69
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- CURPPPMZYPWREO-UHFFFAOYSA-N 2h-3,1-benzothiazine Chemical class C1=CC=CC2=NCSC=C21 CURPPPMZYPWREO-UHFFFAOYSA-N 0.000 title claims description 3
- -1 methyl-imino Chemical group 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- 239000002253 acid Substances 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 230000009467 reduction Effects 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 150000002540 isothiocyanates Chemical class 0.000 claims description 11
- 150000007522 mineralic acids Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 235000013877 carbamide Nutrition 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 9
- 235000005985 organic acids Nutrition 0.000 claims description 9
- 150000003585 thioureas Chemical class 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 150000005130 benzoxazines Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052945 inorganic sulfide Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010306 acid treatment Methods 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- APIDZBPYFWRUMX-UHFFFAOYSA-N 5-chloro-4-phenyl-4H-3,1-benzothiazin-2-amine Chemical compound NC1=NC2=C(C(S1)C1=CC=CC=C1)C(=CC=C2)Cl APIDZBPYFWRUMX-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000506 psychotropic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- OBJKBAIJJMUPHZ-UHFFFAOYSA-N 4-methyl-4H-3,1-benzothiazin-2-amine Chemical compound NC1=NC2=C(C(S1)C)C=CC=C2 OBJKBAIJJMUPHZ-UHFFFAOYSA-N 0.000 claims 1
- VOTOEFBRXKDJSA-UHFFFAOYSA-N 6-chloro-N-ethyl-4-(4-methoxyphenyl)-1,4-dihydro-3,1-benzothiazin-2-imine Chemical compound C(C)NC1=NC2=C(C(S1)C1=CC=C(C=C1)OC)C=C(C=C2)Cl VOTOEFBRXKDJSA-UHFFFAOYSA-N 0.000 claims 1
- KHNGHBRGVBRUAT-UHFFFAOYSA-N N-ethyl-4-phenyl-1,4-dihydro-3,1-benzothiazin-2-imine Chemical compound C(C)NC1=NC2=C(C(S1)C1=CC=CC=C1)C=CC=C2 KHNGHBRGVBRUAT-UHFFFAOYSA-N 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 207
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 54
- 239000013078 crystal Substances 0.000 description 46
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- 239000002904 solvent Substances 0.000 description 33
- 238000001816 cooling Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 23
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 22
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- 229940073584 methylene chloride Drugs 0.000 description 18
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- 230000008020 evaporation Effects 0.000 description 16
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- 150000001298 alcohols Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
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- 230000000694 effects Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- NAWYZLGDGZTAPN-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanol Chemical class NC1=CC=CC=C1C(O)C1=CC=CC=C1 NAWYZLGDGZTAPN-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 5
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- 239000008101 lactose Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- LASJRIHCUCYPGY-UHFFFAOYSA-N n,n-diethyl-2-isothiocyanatoethanamine Chemical compound CCN(CC)CCN=C=S LASJRIHCUCYPGY-UHFFFAOYSA-N 0.000 description 1
- QPBVKSLJBRCKIF-UHFFFAOYSA-N n,n-diethyl-3-isothiocyanatopropan-1-amine Chemical compound CCN(CC)CCCN=C=S QPBVKSLJBRCKIF-UHFFFAOYSA-N 0.000 description 1
- QBDAQEFPQBHBGM-UHFFFAOYSA-N n-ethyl-4h-3,1-benzothiazin-2-amine Chemical compound C1=CC=C2CSC(NCC)=NC2=C1 QBDAQEFPQBHBGM-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 229960000965 nimesulide Drugs 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N o-aminobenzyl alcohol Natural products NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 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
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
-
- 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (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 Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Check Valves (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046229 | 1965-06-03 | ||
| DEF0048687 | 1966-03-18 | ||
| DEF0048726 | 1966-03-22 | ||
| DEF0048739 | 1966-03-23 | ||
| DEF0048738 | 1966-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25858A true IL25858A (en) | 1971-01-28 |
Family
ID=27512066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25858A IL25858A (en) | 1965-06-03 | 1966-05-27 | 3,1-benzothiazines and 3,1-benzoxazines,process for preparing them and compositions thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3417085A (is") |
| BE (1) | BE682070A (is") |
| BR (1) | BR6680180D0 (is") |
| CH (1) | CH496724A (is") |
| DE (5) | DE1545820A1 (is") |
| ES (1) | ES327432A1 (is") |
| FR (2) | FR5710M (is") |
| GB (1) | GB1152486A (is") |
| IL (1) | IL25858A (is") |
| NL (1) | NL6607386A (is") |
| NO (1) | NO119681B (is") |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670772C3 (de) * | 1966-11-24 | 1978-04-20 | Hoechst Ag, 6000 Frankfurt | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
| DE1670773A1 (de) * | 1966-11-26 | 1970-12-23 | Hoechst Ag | Verfahren zur Herstellung von 3,1-Benzothiazin-Derivaten |
| US4005082A (en) * | 1967-09-25 | 1977-01-25 | Gruppo Lepetit S.P.A. | 1H-2,3-Benzoxazines |
| US4002620A (en) * | 1975-10-30 | 1977-01-11 | Morton-Norwich Products, Inc. | 2-Anilino-4H-3,1-benzothiazines |
| US4002622A (en) * | 1975-10-30 | 1977-01-11 | Morton-Norwich Products, Inc. | 2-(3-Chloroanilino)-4H-3,1-benzothiazine |
| US4002621A (en) * | 1975-10-30 | 1977-01-11 | Morton-Norwich Products, Inc. | 6-Chloro-2-(3,4-dichloroanilino)-4H-3,1-benzothiazine |
| JPS5277132A (en) * | 1975-12-23 | 1977-06-29 | Fuji Photo Film Co Ltd | Preparation of thiazine derivative |
| JPS593279B2 (ja) * | 1976-02-04 | 1984-01-23 | 富士写真フイルム株式会社 | 記録材料 |
| US4214889A (en) * | 1977-10-07 | 1980-07-29 | Sandoz, Inc. | Benzoxazine herbicides |
| US4164407A (en) * | 1977-10-07 | 1979-08-14 | Sandoz, Inc. | Benzoxazine herbicides |
| DE3375012D1 (en) * | 1982-06-25 | 1988-02-04 | Shell Int Research | Herbicidal urea compounds |
| FR2625798B1 (fr) * | 1988-01-08 | 1990-07-06 | Perez Benoit | Ballon de production d'eau chaude et procede de mise en chauffe dudit ballon |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168517A (en) * | 1965-02-02 | Novel z-phenylamino-x |
-
1965
- 1965-06-03 DE DE19651545820 patent/DE1545820A1/de active Pending
-
1966
- 1966-03-18 DE DE19661670677 patent/DE1670677A1/de active Pending
- 1966-03-22 DE DE1670679A patent/DE1670679C3/de not_active Expired
- 1966-03-23 DE DE19661670680 patent/DE1670680A1/de active Pending
- 1966-03-23 DE DE19661670681 patent/DE1670681A1/de active Pending
- 1966-05-24 US US552416A patent/US3417085A/en not_active Expired - Lifetime
- 1966-05-27 IL IL25858A patent/IL25858A/en unknown
- 1966-05-27 NL NL6607386A patent/NL6607386A/xx unknown
- 1966-05-31 CH CH783566A patent/CH496724A/de not_active IP Right Cessation
- 1966-06-01 ES ES0327432A patent/ES327432A1/es not_active Expired
- 1966-06-02 NO NO163275A patent/NO119681B/no unknown
- 1966-06-03 BR BR180180/66A patent/BR6680180D0/pt unknown
- 1966-06-03 GB GB24865/66A patent/GB1152486A/en not_active Expired
- 1966-06-03 BE BE682070D patent/BE682070A/xx unknown
- 1966-09-02 FR FR75103A patent/FR5710M/fr not_active Expired
- 1966-09-02 FR FR75102A patent/FR5709M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES327432A1 (es) | 1967-10-16 |
| DE1545820A1 (de) | 1969-12-11 |
| US3417085A (en) | 1968-12-17 |
| BR6680180D0 (pt) | 1973-12-26 |
| DE1670677A1 (de) | 1970-05-06 |
| CH496724A (de) | 1970-09-30 |
| DE1670679A1 (de) | 1970-08-06 |
| NO119681B (is") | 1970-06-22 |
| FR5709M (is") | 1968-01-15 |
| DE1670680A1 (de) | 1970-06-11 |
| DE1670679B2 (de) | 1973-03-22 |
| DE1670679C3 (de) | 1973-10-18 |
| NL6607386A (is") | 1966-12-05 |
| GB1152486A (en) | 1969-05-21 |
| BE682070A (is") | 1966-12-05 |
| FR5710M (is") | 1968-01-15 |
| DE1670681A1 (de) | 1970-08-20 |
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