NL8201642A - Nieuwe bicyclische dioxazaverbindingen alsmede werkwijze ter bereiding van deze verbindingen en de therapeutische toepassing daarvan. - Google Patents
Nieuwe bicyclische dioxazaverbindingen alsmede werkwijze ter bereiding van deze verbindingen en de therapeutische toepassing daarvan. Download PDFInfo
- Publication number
- NL8201642A NL8201642A NL8201642A NL8201642A NL8201642A NL 8201642 A NL8201642 A NL 8201642A NL 8201642 A NL8201642 A NL 8201642A NL 8201642 A NL8201642 A NL 8201642A NL 8201642 A NL8201642 A NL 8201642A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- compounds
- group
- compound
- benzyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 107
- 238000000034 method Methods 0.000 title claims description 26
- 230000001225 therapeutic effect Effects 0.000 title description 4
- -1 methoxy, hydroxy Chemical group 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000008366 benzophenones Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006276 transfer reaction Methods 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- DAMCMDLXUQISAV-UHFFFAOYSA-N 3-benzyl-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane Chemical compound C=1C=CC=CC=1CN(C1)CC(O2)COC12C1=CC=CC=C1 DAMCMDLXUQISAV-UHFFFAOYSA-N 0.000 description 2
- DLUVFLJGSOUCPL-UHFFFAOYSA-N 3-benzyl-7-(4-fluorophenyl)-8,10-dioxa-3-azabicyclo[5.2.1]decane Chemical compound C(C1=CC=CC=C1)N1CC2COC(CCC1)(O2)C2=CC=C(C=C2)F DLUVFLJGSOUCPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- KDAPLNKNJBQQBX-BTJKTKAUSA-N (Z)-but-2-enedioic acid 5-(4-fluorophenyl)-3-methyl-6,8-dioxa-3-azabicyclo[3.2.1]octane Chemical compound OC(=O)\C=C/C(O)=O.C1N(C)CC(O2)COC12C1=CC=C(F)C=C1 KDAPLNKNJBQQBX-BTJKTKAUSA-N 0.000 description 1
- NJYBVFSXBDLXHH-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanamine Chemical compound NCC1COCO1 NJYBVFSXBDLXHH-UHFFFAOYSA-N 0.000 description 1
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- IKZOMJGRWIOEDP-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxolane Chemical compound ClCC1OCCO1 IKZOMJGRWIOEDP-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-VKHMYHEASA-N 3-aminopropane-1,2-diol Chemical compound NC[C@H](O)CO KQIGMPWTAHJUMN-VKHMYHEASA-N 0.000 description 1
- TZIXQRFRGGOPHI-UHFFFAOYSA-N 3-benzyl-5-pyridin-3-yl-6,8-dioxa-3-azabicyclo[3.2.1]octane Chemical compound C=1C=CC=CC=1CN(C1)CC(O2)COC12C1=CC=CN=C1 TZIXQRFRGGOPHI-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HPHTWLVECJQIFO-UHFFFAOYSA-N 5-pyridin-3-yl-6,8-dioxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC(O2)COC21C1=CC=CN=C1 HPHTWLVECJQIFO-UHFFFAOYSA-N 0.000 description 1
- BWDZOARHBYZCEY-UHFFFAOYSA-N COS(=O)(=O)OC.O=CN1CCOCC1 Chemical compound COS(=O)(=O)OC.O=CN1CCOCC1 BWDZOARHBYZCEY-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
- FYGHNUOSAMTKMA-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.C1C(O2)COC2(C(C)(C)C)CN1CC1=CC=CC=C1 Chemical compound OC(=O)\C=C/C(O)=O.C1C(O2)COC2(C(C)(C)C)CN1CC1=CC=CC=C1 FYGHNUOSAMTKMA-BTJKTKAUSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 description 1
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 1
- LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- RMBGFUOEZINVEP-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;phenol Chemical compound OC1=CC=CC=C1.O=C1C=CC(=O)C=C1 RMBGFUOEZINVEP-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 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
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8107904A FR2504141A1 (fr) | 1981-04-21 | 1981-04-21 | Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique |
| FR8107904 | 1981-04-21 | ||
| FR8205553A FR2524469A2 (fr) | 1982-03-31 | 1982-03-31 | Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique |
| FR8205553 | 1982-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8201642A true NL8201642A (nl) | 1982-11-16 |
Family
ID=26222343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8201642A NL8201642A (nl) | 1981-04-21 | 1982-04-20 | Nieuwe bicyclische dioxazaverbindingen alsmede werkwijze ter bereiding van deze verbindingen en de therapeutische toepassing daarvan. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4463004A (cs) |
| AU (1) | AU8284582A (cs) |
| DE (1) | DE3214570A1 (cs) |
| ES (1) | ES512108A0 (cs) |
| GB (1) | GB2096998B (cs) |
| GR (1) | GR75910B (cs) |
| IT (1) | IT1190782B (cs) |
| LU (1) | LU84100A1 (cs) |
| NL (1) | NL8201642A (cs) |
| SE (1) | SE8202364L (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITFI20020107A1 (it) * | 2002-06-19 | 2003-12-19 | Antonio Guarna | Composizioni farmaceutiche atte all'uso nel trattamento di patologie correlate all'azione di neutrofine e composti attivi in esse contenuti |
| ITFI20120062A1 (it) | 2012-03-21 | 2013-09-22 | Minerva Patents S A | Componenti per il trattamento di malattie correlate a ischemia-riperfusione. |
-
1982
- 1982-04-13 GR GR67899A patent/GR75910B/el unknown
- 1982-04-15 SE SE8202364A patent/SE8202364L/xx not_active Application Discontinuation
- 1982-04-16 US US06/368,924 patent/US4463004A/en not_active Expired - Fee Related
- 1982-04-16 GB GB8211124A patent/GB2096998B/en not_active Expired
- 1982-04-20 ES ES512108A patent/ES512108A0/es active Granted
- 1982-04-20 NL NL8201642A patent/NL8201642A/nl not_active Application Discontinuation
- 1982-04-20 AU AU82845/82A patent/AU8284582A/en not_active Abandoned
- 1982-04-20 LU LU84100A patent/LU84100A1/fr unknown
- 1982-04-20 DE DE19823214570 patent/DE3214570A1/de not_active Withdrawn
- 1982-04-20 IT IT20819/82A patent/IT1190782B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1190782B (it) | 1988-02-24 |
| GB2096998B (en) | 1985-04-24 |
| AU8284582A (en) | 1982-10-28 |
| GR75910B (cs) | 1984-08-02 |
| GB2096998A (en) | 1982-10-27 |
| SE8202364L (sv) | 1982-10-22 |
| IT8220819A0 (it) | 1982-04-20 |
| DE3214570A1 (de) | 1982-12-30 |
| ES8307253A1 (es) | 1983-07-01 |
| LU84100A1 (fr) | 1982-09-13 |
| ES512108A0 (es) | 1983-07-01 |
| US4463004A (en) | 1984-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE457258B (sv) | Nya 5-aminometyl-3-aryl-2-oxazolidinoner, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner | |
| CA1288102C (en) | Pyridine derivatives, their preparation and their use | |
| Skell et al. | Synthesis and Properties of Alkylpyrroles | |
| Ayad et al. | Asymmetric syntheses of (−)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate | |
| JPS6141917B2 (cs) | ||
| Diana et al. | Structure-activity studies of 5-[[4-(4, 5-dihydro-2-oxazolyl) phenoxy] alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating | |
| NL8201642A (nl) | Nieuwe bicyclische dioxazaverbindingen alsmede werkwijze ter bereiding van deze verbindingen en de therapeutische toepassing daarvan. | |
| HU181147B (en) | Process for preparing substituted heterocyclin phenoxamines | |
| BG63917B1 (bg) | 1-ар(алк)ил-имидазолин-2-они с дизаместен аминов остатък на 4-място, с антиконвулсивно действие и метод за получаването им | |
| US2504977A (en) | Chlorethyl dibenzyl quaternary ammonium compound | |
| IE52259B1 (en) | Thiazoline derivatives,processes for their preparation,their use and pharmaceutical preparations containing these compounds | |
| LU82677A1 (fr) | Nouveaux derives de la 3,4,5-trimethoxy cinnamoyle piperazine,leur procede de preparation et leur application en therapeutique | |
| US3332949A (en) | 1-phenyl-4-[2-(2-pyridyl)-ethyl] piperazines | |
| US2980693A (en) | Methods for producing same | |
| JPH0665269A (ja) | ホスホン酸ジエステル誘導体 | |
| US4528380A (en) | 5-(1-Propyl)n-butyl tetrazoles | |
| JPS63225354A (ja) | アゼチジノン誘導体 | |
| Aguirre et al. | Structure and stereochemistry of cyclodimers obtained by acid treatment of trans-stilbenes and of N-1, 2-diarylethylamides | |
| US3119829A (en) | 5-tropinyl dibenzocycloheptene derivatives | |
| CN114685325B (zh) | 一种含胺化合物及其制备方法和用途 | |
| JPH0565238A (ja) | 新規な化合物及び分離剤 | |
| AU603081B2 (en) | Symmetrical O-substituted dioximes of benzo-fused beta- diketocycloalkylenes, the processes for their preparation and their application as drugs | |
| US4631277A (en) | Hexahydrodibenzodioxane compounds and pharmaceutical compositions | |
| SU528870A3 (ru) | Способ получени производных 2-имидазолидинона или их солей | |
| US3265711A (en) | Aminotetrahydrofuryl esters |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |