AU599312B2 - Method for treating muscle tension, muscle spasticity and anxiety with 3-aryloxy-azetidinecarboxamides - Google Patents
Method for treating muscle tension, muscle spasticity and anxiety with 3-aryloxy-azetidinecarboxamides Download PDFInfo
- Publication number
- AU599312B2 AU599312B2 AU53888/86A AU5388886A AU599312B2 AU 599312 B2 AU599312 B2 AU 599312B2 AU 53888/86 A AU53888/86 A AU 53888/86A AU 5388886 A AU5388886 A AU 5388886A AU 599312 B2 AU599312 B2 AU 599312B2
- Authority
- AU
- Australia
- Prior art keywords
- trifluoromethyl
- phenoxy
- azetidine
- carboxamide
- azetidinecarboxamide
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 41
- 208000019901 Anxiety disease Diseases 0.000 title claims description 12
- 230000036506 anxiety Effects 0.000 title claims description 12
- 206010049816 Muscle tightness Diseases 0.000 title claims description 9
- 208000008238 Muscle Spasticity Diseases 0.000 title claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 61
- 238000004458 analytical method Methods 0.000 claims description 61
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 59
- 239000000047 product Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000013078 crystal Substances 0.000 claims description 41
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 14
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- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 210000003205 muscle Anatomy 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
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- ZUTYSNQEFFGMKG-UHFFFAOYSA-N n-prop-2-enyl-3-pyridin-2-yloxyazetidine-1-carboxamide Chemical compound C1N(C(=O)NCC=C)CC1OC1=CC=CC=N1 ZUTYSNQEFFGMKG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
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- YTRPOSQFCMQDPK-UHFFFAOYSA-N 3-(3-chlorophenoxy)azetidine-1-carboxamide Chemical compound C1N(C(=O)N)CC1OC1=CC=CC(Cl)=C1 YTRPOSQFCMQDPK-UHFFFAOYSA-N 0.000 claims description 2
- PXHQIJBXGKVVEN-UHFFFAOYSA-N 3-pyridin-2-yloxyazetidine-1-carboxamide Chemical compound C1N(C(=O)N)CC1OC1=CC=CC=N1 PXHQIJBXGKVVEN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 1
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- BGNVRWKCNDRXDE-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)N)CC1OC1=CC=C(C(F)(F)F)C=C1 BGNVRWKCNDRXDE-UHFFFAOYSA-N 0.000 claims 1
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
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- SEALWFDYCNCLNY-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NCC2CC2)=C1 SEALWFDYCNCLNY-UHFFFAOYSA-N 0.000 claims 1
- XYTDLEDSAYYSHI-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carbothioamide Chemical compound C1N(C(=S)NCCCN(CC)CC)CC1OC1=CC=CC(C(F)(F)F)=C1 XYTDLEDSAYYSHI-UHFFFAOYSA-N 0.000 claims 1
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- JTFRITVGJZKYBU-UHFFFAOYSA-N n-phenyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NC=2C=CC=CC=2)=C1 JTFRITVGJZKYBU-UHFFFAOYSA-N 0.000 claims 1
- GACNVLGLEIQNGN-UHFFFAOYSA-N n-phenyl-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)NC=2C=CC=CC=2)C1 GACNVLGLEIQNGN-UHFFFAOYSA-N 0.000 claims 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229960004715 morphine sulfate Drugs 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- GUOONOJYWQOJJP-DCMFLLSESA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]-3-[methyl(methylsulfonyl)amino]-5-[(2r)-2-(4-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carbonyl]benzamide Chemical compound C1([C@H]2CCCN2C(=O)C=2C=C(C=C(C=2)N(C)S(C)(=O)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(OC(F)(F)F)C=CC=2)=NC(C)=CS1 GUOONOJYWQOJJP-DCMFLLSESA-N 0.000 description 1
- CZGNWJWETXWLMW-UHFFFAOYSA-N n-methyl-3-phenoxyazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1OC1=CC=CC=C1 CZGNWJWETXWLMW-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-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
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LJPYJRMMPVFEKR-UHFFFAOYSA-N prop-2-ynylurea Chemical compound NC(=O)NCC#C LJPYJRMMPVFEKR-UHFFFAOYSA-N 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70663285A | 1985-02-28 | 1985-02-28 | |
| US706632 | 1985-02-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5388886A AU5388886A (en) | 1986-09-04 |
| AU599312B2 true AU599312B2 (en) | 1990-07-19 |
Family
ID=24838427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU53888/86A Ceased AU599312B2 (en) | 1985-02-28 | 1986-02-21 | Method for treating muscle tension, muscle spasticity and anxiety with 3-aryloxy-azetidinecarboxamides |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3641343A1 (de) * | 1986-12-03 | 1988-06-16 | Hoechst Ag | Carbamoylimidazol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| JP5624894B2 (ja) * | 2008-03-04 | 2014-11-12 | ヴァーナリスアールアンドディー リミテッドＶｅｒｎａｌｉｓ Ｒ＆Ｄ Ｌｉｍｉｔｅｄ | アゼチジン誘導体 |
| CN113754541B (zh) * | 2020-06-02 | 2025-01-03 | 深圳湾实验室 | 靶向eb病毒核抗原蛋白的小分子抑制剂、制备方法及其应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226861A (en) * | 1978-04-18 | 1980-10-07 | A. H. Robins Company, Inc. | N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides |
| AU553528B2 (en) * | 1982-08-19 | 1986-07-17 | A.H. Robins Company, Incorporated | 3-phenoxy-1-acetidine carboxamides |
| AU569307B2 (en) * | 1983-07-06 | 1988-01-28 | A.H. Robins Company, Incorporated | 3-phenoxy-1-azetidinecarboxamides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505907A (en) * | 1982-09-02 | 1985-03-19 | A. H. Robins Company, Inc. | N-Formyl and N-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides |
-
1986
- 1986-02-10 IN IN90/MAS/86A patent/IN162808B/en unknown
- 1986-02-18 ZA ZA861215A patent/ZA861215B/xx unknown
- 1986-02-21 AU AU53888/86A patent/AU599312B2/en not_active Ceased
- 1986-02-25 GR GR860531A patent/GR860531B/el unknown
- 1986-02-26 PH PH33452A patent/PH25525A/en unknown
- 1986-02-26 IL IL7799586A patent/IL77995A/xx not_active IP Right Cessation
- 1986-02-27 DK DK90186A patent/DK168422B1/da not_active IP Right Cessation
- 1986-02-27 NZ NZ21531286A patent/NZ215312A/xx unknown
- 1986-02-27 CA CA000502877A patent/CA1294274C/en not_active Expired - Lifetime
- 1986-02-27 ES ES552472A patent/ES8802300A1/es not_active Expired
- 1986-02-28 JP JP61043906A patent/JPH0699386B2/ja not_active Expired - Lifetime
- 1986-02-28 PT PT8211886A patent/PT82118B/pt not_active IP Right Cessation
-
1993
- 1993-03-29 DK DK36893A patent/DK170270B1/da not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226861A (en) * | 1978-04-18 | 1980-10-07 | A. H. Robins Company, Inc. | N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides |
| AU553528B2 (en) * | 1982-08-19 | 1986-07-17 | A.H. Robins Company, Incorporated | 3-phenoxy-1-acetidine carboxamides |
| AU569307B2 (en) * | 1983-07-06 | 1988-01-28 | A.H. Robins Company, Incorporated | 3-phenoxy-1-azetidinecarboxamides |
Also Published As
| Publication number | Publication date |
|---|---|
| DK168422B1 (da) | 1994-03-28 |
| CA1294274C (en) | 1992-01-14 |
| DK36893A (da) | 1993-03-29 |
| IL77995A (en) | 1989-06-30 |
| PH25525A (en) | 1991-07-24 |
| JPS61205254A (ja) | 1986-09-11 |
| NZ215312A (en) | 1990-02-26 |
| AU5388886A (en) | 1986-09-04 |
| DK90186D0 (da) | 1986-02-27 |
| DK170270B1 (da) | 1995-07-24 |
| IN162808B (enrdf_load_stackoverflow) | 1988-07-09 |
| DK36893D0 (da) | 1993-03-29 |
| GR860531B (en) | 1986-06-24 |
| JPH0699386B2 (ja) | 1994-12-07 |
| ES8802300A1 (es) | 1987-05-01 |
| PT82118A (en) | 1986-03-01 |
| DK90186A (da) | 1986-08-29 |
| PT82118B (pt) | 1988-07-01 |
| ZA861215B (en) | 1986-10-29 |
| ES552472A0 (es) | 1987-05-01 |
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