FR2504141A1 - Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2504141A1 FR2504141A1 FR8107904A FR8107904A FR2504141A1 FR 2504141 A1 FR2504141 A1 FR 2504141A1 FR 8107904 A FR8107904 A FR 8107904A FR 8107904 A FR8107904 A FR 8107904A FR 2504141 A1 FR2504141 A1 FR 2504141A1
- Authority
- FR
- France
- Prior art keywords
- sep
- formula
- compounds
- benzyl
- cyclohexyl
- 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.)
- Granted
Links
- 229940035676 analgesics Drugs 0.000 title abstract description 3
- 239000000730 antalgic agent Substances 0.000 title abstract description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 title 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 title 1
- 239000004914 cyclooctane Substances 0.000 title 1
- 239000002243 precursor Substances 0.000 title 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 16
- -1 methoxy, hydroxy Chemical group 0.000 abstract description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 10
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 125000001544 thienyl group Chemical group 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 241000699670 Mus sp. Species 0.000 abstract description 2
- 230000001154 acute effect Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000007912 intraperitoneal administration Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-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
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229940049920 malate Drugs 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 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
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- BWDZOARHBYZCEY-UHFFFAOYSA-N COS(=O)(=O)OC.O=CN1CCOCC1 Chemical compound COS(=O)(=O)OC.O=CN1CCOCC1 BWDZOARHBYZCEY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000005905 mesyloxy group Chemical group 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- OSANFONRYANBRD-BTJKTKAUSA-N (z)-but-2-enedioic acid;octane Chemical compound CCCCCCCC.OC(=O)\C=C/C(O)=O OSANFONRYANBRD-BTJKTKAUSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- JGUBUNDASUIZIB-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)CC(=O)N1CCCC1 JGUBUNDASUIZIB-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
- BIANZVZZKGIQKG-UHFFFAOYSA-N 4-[4-(5-hydroxypentoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 BIANZVZZKGIQKG-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 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
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000202 analgesic effect Effects 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
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 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
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SFLLRHHQOUHDKK-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydro-3ah-di[1,3]dioxolo[5,4-a:5',4'-d]pyran-5-carboxamide Chemical compound C1=C(F)C(C)=CC=C1NC(=O)C1C2OC(C)(C)OC2C2OC(C)(C)OC2O1 SFLLRHHQOUHDKK-UHFFFAOYSA-N 0.000 description 1
- RNIOLUYSZZRASJ-UHFFFAOYSA-N n-(3-fluorophenyl)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydro-3ah-di[1,3]dioxolo[5,4-a:5',4'-d]pyran-5-carboxamide Chemical compound C12OC(C)(C)OC2C2OC(C)(C)OC2OC1C(=O)NC1=CC=CC(F)=C1 RNIOLUYSZZRASJ-UHFFFAOYSA-N 0.000 description 1
- MORYQQDCTDTLST-UHFFFAOYSA-N n-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine Chemical compound O1C(C)(C)OCC1CNCC1=CC=CC=C1 MORYQQDCTDTLST-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (14)
| 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 |
| GR67899A GR75910B (OSRAM) | 1981-04-21 | 1982-04-13 | |
| BE0/207826A BE892853A (fr) | 1981-04-21 | 1982-04-15 | Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique |
| SE8202364A SE8202364L (sv) | 1981-04-21 | 1982-04-15 | Nya dioxazabicykliska derivat, deras framstellningssett och deras terapeutiska anvending |
| GB8211124A GB2096998B (en) | 1981-04-21 | 1982-04-16 | Dioxaazabicyclic compounds |
| US06/368,924 US4463004A (en) | 1981-04-21 | 1982-04-16 | Dioxazabicyclic derivatives |
| ZA822639A ZA822639B (en) | 1981-04-21 | 1982-04-19 | New dioxazabicyclic derivatives,a process for preparation thereof and the application of same in therapeutics |
| DE19823214570 DE3214570A1 (de) | 1981-04-21 | 1982-04-20 | Neuartige dioxazabicyklische derivate, ihr herstellungsverfahren und ihre anwendung in der therapie |
| IT20819/82A IT1190782B (it) | 1981-04-21 | 1982-04-20 | Derivati diossazabiciclici,loro procedimento di preparazione e loro applicazione in terapia |
| JP57064723A JPS57188593A (en) | 1981-04-21 | 1982-04-20 | Novel dioxazabicyclo derivative, manufacture and drug |
| ES512108A ES8307253A1 (es) | 1981-04-21 | 1982-04-20 | "procedimiento para la preparacion de nuevos derivados dioxazabiciclicos". |
| NL8201642A NL8201642A (nl) | 1981-04-21 | 1982-04-20 | Nieuwe bicyclische dioxazaverbindingen alsmede werkwijze ter bereiding van deze verbindingen en de therapeutische toepassing daarvan. |
| AU82845/82A AU8284582A (en) | 1981-04-21 | 1982-04-20 | Dioxazabicyclic derivatives |
| LU84100A LU84100A1 (fr) | 1981-04-21 | 1982-04-20 | Nouveaux derives dioxazabicycliques,leur procede de preparation et leur application en therapeutique |
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2504141A1 true FR2504141A1 (fr) | 1982-10-22 |
| FR2504141B1 FR2504141B1 (OSRAM) | 1983-12-30 |
Family
ID=9257613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8107904A Granted FR2504141A1 (fr) | 1981-04-21 | 1981-04-21 | Nouveaux derives dioxazabicycliques, leur procede de preparation et leur application en therapeutique |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57188593A (OSRAM) |
| BE (1) | BE892853A (OSRAM) |
| FR (1) | FR2504141A1 (OSRAM) |
| ZA (1) | ZA822639B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1130022B1 (en) * | 2000-02-29 | 2009-07-22 | Universita Degli Studi di Firenze | 3-Aza-6,8-dioxabicyclo[3.2.1]octanes and analogues and combinatorial libraries containing them |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046892A (en) * | 1976-03-24 | 1977-09-06 | Abbott Laboratories | 7-Aza-11,12-Dioxa-6-phenyl-tricyclo[7,2,1,01.6 ]dodecane derivatives and process for their preparation |
-
1981
- 1981-04-21 FR FR8107904A patent/FR2504141A1/fr active Granted
-
1982
- 1982-04-15 BE BE0/207826A patent/BE892853A/fr not_active IP Right Cessation
- 1982-04-19 ZA ZA822639A patent/ZA822639B/xx unknown
- 1982-04-20 JP JP57064723A patent/JPS57188593A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046892A (en) * | 1976-03-24 | 1977-09-06 | Abbott Laboratories | 7-Aza-11,12-Dioxa-6-phenyl-tricyclo[7,2,1,01.6 ]dodecane derivatives and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA822639B (en) | 1983-03-30 |
| BE892853A (fr) | 1982-10-15 |
| FR2504141B1 (OSRAM) | 1983-12-30 |
| JPS57188593A (en) | 1982-11-19 |
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