NO115110B - - Google Patents
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- Publication number
- NO115110B NO115110B NO150693A NO15069363A NO115110B NO 115110 B NO115110 B NO 115110B NO 150693 A NO150693 A NO 150693A NO 15069363 A NO15069363 A NO 15069363A NO 115110 B NO115110 B NO 115110B
- Authority
- NO
- Norway
- Prior art keywords
- group
- beta
- diphenyl
- formula
- lower alkoxy
- Prior art date
Links
- 239000000047 product Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 aminophenyl group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- ITADKRUBBFYKGM-UHFFFAOYSA-N 5-(3-chloropropyl)-3-(2,2-diphenylethyl)-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C(CC1=NOC(=N1)CCCCl)C1=CC=CC=C1 ITADKRUBBFYKGM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- ONTOFAWPPHNLML-UHFFFAOYSA-N 3-(2,2-diphenylethyl)-5-(2-piperidin-1-ylethyl)-1,2,4-oxadiazole;hydron;chloride Chemical compound Cl.C1CCCCN1CCC(ON=1)=NC=1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ONTOFAWPPHNLML-UHFFFAOYSA-N 0.000 description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000003434 antitussive agent Substances 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- UCKPDEJTQRIACH-UHFFFAOYSA-N 3-piperidin-1-ylpropanoyl chloride Chemical compound ClC(=O)CCN1CCCCC1 UCKPDEJTQRIACH-UHFFFAOYSA-N 0.000 description 1
- FKDQTDYQVLBNOU-UHFFFAOYSA-N 4-[3-[3-(2,2-diphenylethyl)-1,2,4-oxadiazol-5-yl]propyl]morpholine Chemical compound C1(=CC=CC=C1)C(CC1=NOC(=N1)CCCN1CCOCC1)C1=CC=CC=C1 FKDQTDYQVLBNOU-UHFFFAOYSA-N 0.000 description 1
- RDERUAPIINCJLO-UHFFFAOYSA-N C1(=CC=CC=C1)C(CC1=NOC(=N1)CCl)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(CC1=NOC(=N1)CCl)C1=CC=CC=C1 RDERUAPIINCJLO-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Chemical class 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MPAWVDTVWPPKJQ-UHFFFAOYSA-N ethyl 3-piperidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCCC1 MPAWVDTVWPPKJQ-UHFFFAOYSA-N 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000003801 laryngeal nerve Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PXZDWASDNFWKSD-UHFFFAOYSA-N prenoxdiazine Chemical compound C1CCCCN1CCC(ON=1)=NC=1CC(C=1C=CC=CC=1)C1=CC=CC=C1 PXZDWASDNFWKSD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GDJWAYOMFZFOTG-UHFFFAOYSA-M sodium;5-cyclohex-2-en-1-yl-5-prop-2-enyl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].O=C1NC([S-])=NC(=O)C1(CC=C)C1C=CCCC1 GDJWAYOMFZFOTG-UHFFFAOYSA-M 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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)
- 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)
- Sawing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000437 | 1963-03-22 | ||
| HUCI000438 | 1963-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115110B true NO115110B (da) | 1968-07-29 |
Family
ID=26318371
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO150693A NO115110B (da) | 1963-03-22 | 1963-11-05 | |
| NO152512A NO118067B (da) | 1963-03-22 | 1964-03-19 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO152512A NO118067B (da) | 1963-03-22 | 1964-03-19 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3265692A (da) |
| BE (2) | BE645478A (da) |
| BR (2) | BR6457780D0 (da) |
| CH (3) | CH490409A (da) |
| CS (2) | CS152413B2 (da) |
| DE (1) | DE1445603C3 (da) |
| DK (2) | DK136608B (da) |
| FI (2) | FI45977C (da) |
| FR (1) | FR4062M (da) |
| GB (2) | GB1063323A (da) |
| NL (3) | NL6402833A (da) |
| NO (2) | NO115110B (da) |
| SE (2) | SE319481B (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458305A (en) * | 1966-08-24 | 1969-07-29 | Gulf Research Development Co | Bispyridinium compounds as herbicides |
| GB1228142A (da) * | 1967-03-31 | 1971-04-15 | ||
| US3697530A (en) * | 1970-12-31 | 1972-10-10 | Takeda Chemical Industries Ltd | Oxadiazole derivatives |
| DE2860691D1 (en) * | 1977-07-12 | 1981-08-13 | Synthelabo | 1,2,4-oxadiazol derivatives, their preparation and application in pharmaceutical compositions |
| DE2801509A1 (de) * | 1978-01-12 | 1979-07-19 | Schering Ag | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| HU180708B (en) * | 1979-10-11 | 1983-04-29 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new 1,2,4-oxadiazine derivatives |
| HU190377B (en) * | 1982-03-12 | 1986-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing theophyllinyl-alkyl-oxadiazoles |
| IE63906B1 (en) * | 1987-11-13 | 1995-06-14 | Novo Nordisk As | Azabicyclic compounds and their preparation and use |
| US5066662A (en) * | 1990-05-21 | 1991-11-19 | Warner-Lambert Company | Substituted oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones and derivatives thereof acting at muscarinic receptors |
| WO2005060961A2 (en) * | 2003-12-18 | 2005-07-07 | Astrazeneca Ab | Treatment of transient lower esophageal sphincter relaxations (tlesrs) and gastro-esophageal reflux disease (gerd) |
| JP5167484B2 (ja) * | 2007-05-21 | 2013-03-21 | 日本放送協会 | 撮像装置 |
| WO2012024150A1 (en) * | 2010-08-16 | 2012-02-23 | Boehringer Ingelheim International Gmbh | Oxadiazole inhibitors of leukotriene production |
| JP2013544837A (ja) * | 2010-12-03 | 2013-12-19 | アラーガン インコーポレイテッド | スフィンゴシン−１−リン酸（ｓ１ｐ）受容体モジュレーターとしての新規オキシムアゼチジン誘導体 |
| BR112013013648A2 (pt) | 2010-12-03 | 2016-09-06 | Allergan Inc | derivados de fenil oxadiazol como moduladores de receptor de esfingosina-1-fosfato(s1p) |
| BR112013013640A2 (pt) * | 2010-12-03 | 2016-09-13 | Allergan Inc | derivados de oxima como moduladores de receptores de esfingosina-1-fosfato (s1p) |
| CA2819666A1 (en) | 2010-12-03 | 2012-06-07 | Allergan, Inc. | Novel azetidine derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3141019A (en) * | 1964-07-14 | Chaohj |
-
0
- GB GB1053825D patent/GB1053825A/en active Active
- NL NL132134D patent/NL132134C/xx active
- NL NL302339D patent/NL302339A/xx unknown
-
1963
- 1963-11-05 NO NO150693A patent/NO115110B/no unknown
- 1963-11-06 DE DE1445603A patent/DE1445603C3/de not_active Expired
- 1963-11-13 FI FI632211A patent/FI45977C/fi active
- 1963-11-20 CS CS6405A patent/CS152413B2/cs unknown
- 1963-11-28 CH CH634568A patent/CH490409A/de not_active IP Right Cessation
- 1963-11-28 CH CH1456463A patent/CH469731A/de unknown
-
1964
- 1964-01-15 DK DK21464AA patent/DK136608B/da unknown
- 1964-01-20 SE SE659/64A patent/SE319481B/xx unknown
- 1964-03-09 CH CH300564A patent/CH431540A/de unknown
- 1964-03-10 GB GB10059/64A patent/GB1063323A/en not_active Expired
- 1964-03-10 FI FI640509A patent/FI45557C/fi active
- 1964-03-12 DK DK126064AA patent/DK109088C/da active
- 1964-03-17 NL NL6402833A patent/NL6402833A/xx unknown
- 1964-03-19 SE SE03429/64A patent/SE333737B/xx unknown
- 1964-03-19 US US353270A patent/US3265692A/en not_active Expired - Lifetime
- 1964-03-19 NO NO152512A patent/NO118067B/no unknown
- 1964-03-20 BE BE645478D patent/BE645478A/xx unknown
- 1964-03-20 BR BR157780/64A patent/BR6457780D0/pt unknown
- 1964-03-21 CS CS164864A patent/CS154210B2/cs unknown
- 1964-03-24 US US354465A patent/US3280122A/en not_active Expired - Lifetime
- 1964-03-26 FR FR968867A patent/FR4062M/fr not_active Expired
- 1964-03-27 BE BE645822D patent/BE645822A/xx unknown
- 1964-03-30 BR BR157951/64A patent/BR6457951D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI45977C (fi) | 1972-11-10 |
| DK136608B (da) | 1977-10-31 |
| BE645822A (da) | 1964-07-16 |
| GB1063323A (en) | 1967-03-30 |
| DE1445603B2 (de) | 1978-06-15 |
| DE1445620A1 (de) | 1968-12-05 |
| FR4062M (da) | 1966-04-04 |
| DK109088C (da) | 1968-03-18 |
| US3265692A (en) | 1966-08-09 |
| BE645478A (da) | 1964-07-16 |
| NL6402833A (da) | 1964-09-23 |
| SE333737B (da) | 1971-03-29 |
| FI45977B (da) | 1972-07-31 |
| CH490409A (de) | 1970-05-15 |
| CH431540A (de) | 1967-03-15 |
| NO118067B (da) | 1969-11-03 |
| BR6457951D0 (pt) | 1973-04-19 |
| SE319481B (da) | 1970-01-19 |
| GB1053825A (da) | |
| NL132134C (da) | |
| CS152413B2 (da) | 1973-12-19 |
| DK136608C (da) | 1978-04-03 |
| DE1445620B2 (de) | 1975-08-07 |
| DE1445603A1 (de) | 1968-12-05 |
| FI45557C (fi) | 1972-07-10 |
| DE1445603C3 (de) | 1979-03-15 |
| BR6457780D0 (pt) | 1973-08-28 |
| US3280122A (en) | 1966-10-18 |
| NL302339A (da) | |
| CH469731A (de) | 1969-03-15 |
| FI45557B (da) | 1972-04-04 |
| CS154210B2 (da) | 1974-03-29 |
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