NO115110B - - Google Patents

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Info

Publication number: NO115110B
Authority: NO; Norway
Prior art keywords: group; beta; diphenyl; formula; lower alkoxy
Prior art date: 1963-03-22

Application number

NO150693A

Other languages

English (en)

Norwegian (no)

Inventor

G Leszovsky

I Erdelyi

L Tardos

D Korbonits

I Malyata

K Harsanyi

P Kiss

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1963-03-22

Filing date

1963-11-05

Publication date

1968-07-29

1963-11-05 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1968-07-29 Publication of NO115110B publication Critical patent/NO115110B/no

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)

NO150693A 1963-03-22 1963-11-05 NO115110B (cs)

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 (cs)	1968-07-29

Family

ID=26318371

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO150693A NO115110B (cs)	1963-03-22	1963-11-05
NO152512A NO118067B (cs)	1963-03-22	1964-03-19

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO152512A NO118067B (cs)	1963-03-22	1964-03-19

Country Status (13)

Country	Link
US (2)	US3265692A (cs)
BE (2)	BE645478A (cs)
BR (2)	BR6457780D0 (cs)
CH (3)	CH490409A (cs)
CS (2)	CS152413B2 (cs)
DE (1)	DE1445603C3 (cs)
DK (2)	DK136608B (cs)
FI (2)	FI45977C (cs)
FR (1)	FR4062M (cs)
GB (2)	GB1063323A (cs)
NL (3)	NL6402833A (cs)
NO (2)	NO115110B (cs)
SE (2)	SE319481B (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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 (cs) *	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
IL88156A (en) *	1987-11-13	1997-02-18	Novo Nordisk As	Azacyclic compounds their preparation and pharmaceutical compositions containing them
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
MX2013001872A (es) *	2010-08-16	2013-09-02	Boehringer Ingelheim Int	Inhibidores de oxadiazol de la produccion de leucotrieno.
BR112013013649A2 (pt)	2010-12-03	2016-09-06	Allergan Inc	derivados de oxima azetidina como moduladores de receptor 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
CA2819603A1 (en) *	2010-12-03	2012-06-07	Allergan, Inc.	Novel oxime derivatives as sphingosine 1-phosphate (s1p) receptor modulators
US8486918B2 (en)	2010-12-03	2013-07-16	Allergan, Inc.	Phenyl oxadiazole derivatives as sphingosine 1-phosphate (S1P) receptor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3141019A (en) *		1964-07-14		Chaohj

0
- NL NL302339D patent/NL302339A/xx unknown
- GB GB1053825D patent/GB1053825A/en active Active
- NL NL132134D patent/NL132134C/xx active
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 FI FI640509A patent/FI45557C/fi active
- 1964-03-10 GB GB10059/64A patent/GB1063323A/en not_active Expired
- 1964-03-12 DK DK126064AA patent/DK109088C/da active
- 1964-03-17 NL NL6402833A patent/NL6402833A/xx unknown
- 1964-03-19 US US353270A patent/US3265692A/en not_active Expired - Lifetime
- 1964-03-19 NO NO152512A patent/NO118067B/no unknown
- 1964-03-19 SE SE03429/64A patent/SE333737B/xx 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
DE1445603C3 (de)	1979-03-15
SE319481B (cs)	1970-01-19
GB1063323A (en)	1967-03-30
FI45557C (fi)	1972-07-10
US3280122A (en)	1966-10-18
BR6457951D0 (pt)	1973-04-19
GB1053825A (cs)
DE1445603B2 (de)	1978-06-15
CH431540A (de)	1967-03-15
DE1445620A1 (de)	1968-12-05
BR6457780D0 (pt)	1973-08-28
DE1445620B2 (de)	1975-08-07
DK109088C (da)	1968-03-18
BE645822A (cs)	1964-07-16
CS154210B2 (cs)	1974-03-29
NL132134C (cs)
FR4062M (cs)	1966-04-04
DK136608B (da)	1977-10-31
US3265692A (en)	1966-08-09
FI45977C (fi)	1972-11-10
FI45557B (cs)	1972-04-04
CH490409A (de)	1970-05-15
NO118067B (cs)	1969-11-03
NL6402833A (cs)	1964-09-23
NL302339A (cs)
CH469731A (de)	1969-03-15
DE1445603A1 (de)	1968-12-05
SE333737B (cs)	1971-03-29
FI45977B (cs)	1972-07-31
CS152413B2 (cs)	1973-12-19
DK136608C (cs)	1978-04-03
BE645478A (cs)	1964-07-16

Publication	Publication Date	Title
NO115110B (cs)	1968-07-29
US3766180A (en)	1973-10-16	3-heterocyclicamino-4-chloro-1,2,5-thiadiazoles
DK158346B (da)	1990-05-07	Analogifremgangsmaade til fremstilling af 4-amino-5-alkylsulfonyl-o-anisamid-derivater samt 2-methoxy-4-amino-5-alkylsulfonylbenzoesyrer til anvendelse som mellemprodukter ved fremgangsmaaden
NO780558L (no)	1978-08-21	Benzoesyre og dens derivater samt fremgangsmaate til deres fremstilling
NO137440B (no)	1977-11-21	Analogifremgangsm}te for fremstilling av terapeutisk aktive pleuromutiliner
US3078214A (en)	1963-02-19	Treatment of mental disturbances with esters of indoles
NO164349B (no)	1990-06-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-(piperidinyl-alkyl)-karboksamider og deres salter.
NO153530B (no)	1985-12-30	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte heterocykliske benzamider.
US3123618A (en)	1964-03-03	Io-dihydroanthkacene-z
NO163597B (no)	1990-03-19	Styreinnretning for et ett-eller tosporet kjoeretoey.
US3001992A (en)	1961-09-26	S-niteo-z-fubftjewdene
NO151387B (no)	1984-12-17	Innstillingsinnretning for en elektronisk digitalindikator
NO852663L (no)	1986-01-06	Fremgangsmaate ved fremstilling av 3-aminocarbonylmethoxy-5-fenylpyrazol-forbindelser.
NO743347L (cs)	1975-04-21
US4806560A (en)	1989-02-21	Imidazo[4,5-b]pyridin-2-one derivatives
NO127447B (cs)	1973-06-25
KR880001715B1 (ko)	1988-09-08	1-푸릴-3,4-디하이드로이소퀴놀린의 제조방법
US2650230A (en)	1953-08-25	Xanthene-9-carboxylic acid esters of nuclearly alkylated 4-piperidinols and salts thereof
US3086976A (en)	1963-04-23	Benzoic acid derivatives and process for producing same
US3594392A (en)	1971-07-20	Dibenzo(b,e)thiepine-1,1-dioxides
US2927925A (en)	1960-03-08	Scopine and sgopoline esters of alpha
US3378592A (en)	1968-04-16	Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide
NO800660L (no)	1980-09-10	Fremgangsmaate for fremstilling av piperidinderivater
NO137997B (no)	1978-02-27	Analogifremgangsm}te til fremstilling av nye terapeutiske aktive sulfobenzosyreimidosubstituerte laktamer
NO783933L (no)	1979-05-28	Fremgangsmaate for fremstilling av naftalenderivater