CA1169870A - 3-phenoxy-1-azetidines - Google Patents

3-phenoxy-1-azetidines

Info

Publication number: CA1169870A
Authority: CA; Canada
Prior art keywords: salt; phenoxy; formula; azetidine; mole
Prior art date: 1980-10-06
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.): Expired

Application number

CA000423251A

Other languages

English (en)

Inventor

Albert D. Cale, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

AH Robins Co Inc

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.)

1980-10-06

Filing date

1983-03-09

Publication date

1984-06-26

1980-10-06 Priority claimed from CA000361594A external-priority patent/CA1161853A/fr

1983-03-09 Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc

1983-03-09 Priority to CA000423251A priority Critical patent/CA1169870A/fr

1984-06-26 Application granted granted Critical

1984-06-26 Publication of CA1169870A publication Critical patent/CA1169870A/fr

Status Expired legal-status Critical Current

Links

125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 10
CCDAHKDEKOTDGR-UHFFFAOYSA-N 3-phenoxyazetidine Chemical compound C1NCC1OC1=CC=CC=C1 CCDAHKDEKOTDGR-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
GLAMCKIBNCIMFW-UHFFFAOYSA-N 1-benzhydryl-3-phenoxyazetidine Chemical compound C1C(OC=2C=CC=CC=2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GLAMCKIBNCIMFW-UHFFFAOYSA-N 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
230000000694 effects Effects 0.000 abstract description 3
210000003169 central nervous system Anatomy 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 15
239000004480 active ingredient Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000000047 product Substances 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000008101 lactose Substances 0.000 description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
239000008107 starch Substances 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 4
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
235000013539 calcium stearate Nutrition 0.000 description 4
239000008116 calcium stearate Substances 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
208000034308 Grand mal convulsion Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010034759 Petit mal epilepsy Diseases 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
235000009430 Thespesia populnea Nutrition 0.000 description 2
206010043994 Tonic convulsion Diseases 0.000 description 2
208000006633 Tonic-Clonic Epilepsy Diseases 0.000 description 2
208000003554 absence epilepsy Diseases 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
201000002933 epilepsy with generalized tonic-clonic seizures Diseases 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BPSVMSCEJRUNBC-UHFFFAOYSA-N 3-(4-carbamoylphenoxy)-n-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1OC1=CC=C(C(N)=O)C=C1 BPSVMSCEJRUNBC-UHFFFAOYSA-N 0.000 description 1
UMRYPVYCXBBOJV-UHFFFAOYSA-N 3-[2-(trifluoromethyl)phenoxy]azetidine Chemical compound FC(F)(F)C1=CC=CC=C1OC1CNC1 UMRYPVYCXBBOJV-UHFFFAOYSA-N 0.000 description 1
RKANEZKQFZAZHZ-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenoxy]azetidine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CNC1 RKANEZKQFZAZHZ-UHFFFAOYSA-N 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
239000011149 active material Substances 0.000 description 1
-1 alkyl 3-phenoxy-1-azetidine-carboxamides Chemical class 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical compound NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 description 1
239000010951 brass Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical group 0.000 description 1
239000003179 convulsant agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
PZSYSFIBRGYUSH-UHFFFAOYSA-N methanesulfonic acid;3-phenoxyazetidine Chemical compound CS(O)(=O)=O.C1NCC1OC1=CC=CC=C1 PZSYSFIBRGYUSH-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA000423251A 1980-10-06 1983-03-09 3-phenoxy-1-azetidines Expired CA1169870A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000423251A CA1169870A (fr)	1980-10-06	1983-03-09	3-phenoxy-1-azetidines

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000361594A CA1161853A (fr)	1978-04-18	1980-10-06	N-alkyle inferieur 3-phenoxy-1-azetidine- carboxamides
CA000423251A CA1169870A (fr)	1980-10-06	1983-03-09	3-phenoxy-1-azetidines

Publications (1)

Publication Number	Publication Date
CA1169870A true CA1169870A (fr)	1984-06-26

Family

ID=25669158

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000423251A Expired CA1169870A (fr)	1980-10-06	1983-03-09	3-phenoxy-1-azetidines

Country Status (1)

Country	Link
CA (1)	CA1169870A (fr)

1983
- 1983-03-09 CA CA000423251A patent/CA1169870A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-06-26	MKEX	Expiry

Publication	Publication Date	Title
CA1161853A (fr)	1984-02-07	N-alkyle inferieur 3-phenoxy-1-azetidine- carboxamides
DE2928485A1 (de)	1981-01-29	Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen
EP0102740B1 (fr)	1986-11-05	N-Formyl et N-hydroxyméthyl phénoxy-3 azétidinecarboxamides-1, leur préparation et leur usage
EP0163260B1 (fr)	1988-08-03	Nouvelles pyrrolidones substituées, procédé pour leur préparation et médicaments
US4052508A (en)	1977-10-04	Heterocyclic dihydroanthracen imines
DE2601137A1 (de)	1976-07-22	Substituierte perhalogenalkylamidine und herzstimulantien
DE2827907A1 (de)	1979-01-11	Acetylenderivate von aminen
EP0102194B1 (fr)	1986-10-22	Phénoxy-3 azétidinecarboxamides-1, leur usage et leur préparation
EP0008715A1 (fr)	1980-03-19	Phényléthanolamines utilisables dans le traitement des maladies inflammatoires
US4571393A (en)	1986-02-18	3-Phenoxy-1-azetidinecarboxamides
CA1169870A (fr)	1984-06-26	3-phenoxy-1-azetidines
US4379151A (en)	1983-04-05	3-Phenoxyazetidines for anorexigenic activity
AU649302B2 (en)	1994-05-19	Tricyclic pyridone derivative
EP0170861A1 (fr)	1986-02-12	Composés d'aminocarbonylméthoxy-3-phényl-5-pyrazol, procédé de leur préparation et les compositions pharmaceutiques les contenant
DE2749584A1 (de)	1978-05-18	Ueberbrueckte geminale diphenylpiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2166359A1 (de)	1974-03-14	Bis- eckige klammer auf (4-acylamidophenoxy)-alkyl eckige klammer zu -aether und ein verfahren zu ihrer herstellung
EP0068240B1 (fr)	1985-09-25	Acylaminométhyl-2-benzodiazépines-1,4, leur préparation et produits intermédiaires et produit pharmaceutiques qui les contiennent
AU599585B2 (en)	1990-07-26	3-Aryloxyazetidine carboxamides as anticonvulsants and antiepileptics
DD290881A5 (de)	1991-06-13	Neue imidazolidin-derivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten
EP0054839A2 (fr)	1982-06-30	Acylaminométhyl-2 benzodiazépines-1,4, leurs sels, procédé pour leur préparation et médicaments contenant ces composés
EP0560905B1 (fr)	1994-10-19	Carboxamides de 3-[2-chloro-4-(trifluoromethyl)phenoxy]-1-azetidine ayant une action anticonvulsive
DE2743493A1 (de)	1978-04-13	Amine, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2609574A1 (de)	1976-09-23	Monosubstituiertes piperazinderivat, verfahren zu seiner herstellung und es enthaltende arzneimittel
EP0239533B1 (fr)	1992-09-16	Dérivés de la pyridine
DE1950351A1 (de)	1971-04-29	Neue 1-(2-Cyano-5-methylphenoxy)-2-hydroxy-3-alkylaminopropane und Verfahren zu ihrer Herstellung