AU655075B2 - N-alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines - Google Patents
N-alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines Download PDFInfo
- Publication number
- AU655075B2 AU655075B2 AU25370/92A AU2537092A AU655075B2 AU 655075 B2 AU655075 B2 AU 655075B2 AU 25370/92 A AU25370/92 A AU 25370/92A AU 2537092 A AU2537092 A AU 2537092A AU 655075 B2 AU655075 B2 AU 655075B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- phenyl
- alkyl
- pharmaceutically acceptable
- 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
- 125000006308 propyl amino group Chemical group 0.000 title claims abstract description 6
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims abstract description 19
- 229960002748 norepinephrine Drugs 0.000 claims abstract description 18
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000003389 potentiating effect Effects 0.000 claims description 4
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical class NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 3
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- 238000005576 amination reaction Methods 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- IUTPYKBKYDVRDB-UHFFFAOYSA-N n-methyl-3-(2-methylphenyl)sulfanyl-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)SC1=CC=CC=C1C IUTPYKBKYDVRDB-UHFFFAOYSA-N 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/766,993 US5281624A (en) | 1991-09-27 | 1991-09-27 | N-alkyl-3-phenyl-3-(2-substituted phenoxy) propylamines and pharmaceutical use thereof |
| US766993 | 1991-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2537092A AU2537092A (en) | 1993-04-01 |
| AU655075B2 true AU655075B2 (en) | 1994-12-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU25370/92A Ceased AU655075B2 (en) | 1991-09-27 | 1992-09-25 | N-alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines |
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| US6071970A (en) * | 1993-02-08 | 2000-06-06 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6017965A (en) * | 1993-02-08 | 2000-01-25 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US7087765B2 (en) * | 1995-06-07 | 2006-08-08 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| TW344661B (en) * | 1993-11-24 | 1998-11-11 | Lilly Co Eli | Pharmaceutical composition for treatment of incontinence |
| WO1997003665A1 (en) * | 1995-07-24 | 1997-02-06 | Eli Lilly And Company | Treatment of attention-deficit/hyperactivity disorder |
| AU4421697A (en) * | 1996-09-19 | 1998-04-14 | American Home Products Corporation | Method of treating urinary incontinence |
| PT1069900E (pt) * | 1998-04-09 | 2005-10-31 | Pharmacia & Upjohn Co Llc | Novos tratamentos para disturbios nervosos |
| US6586427B2 (en) | 1998-04-09 | 2003-07-01 | Pharmacia & Upjohn Company | Treatments for nervous disorders |
| US6342533B1 (en) | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| HUP0200898A3 (en) | 1999-04-06 | 2005-09-28 | Sepracor Inc | Derivatives of venlafaxine and methods of preparing and using the same |
| NZ516111A (en) * | 1999-05-24 | 2003-05-30 | Mitsubishi Pharma Corp | Phenoxypropylamine compounds useful to treat depression |
| KR20090087135A (ko) * | 1999-07-01 | 2009-08-14 | 파마시아 앤드 업존 캄파니 엘엘씨 | 고선택성 노르에피네프린 재흡수 억제제 및 그의 이용 방법 |
| US20040034106A1 (en) * | 2001-11-06 | 2004-02-19 | Read Holly Ann | Treatment of anxiety disorders |
| WO2003047560A1 (en) * | 2001-11-30 | 2003-06-12 | Eli Lilly And Company | Use of norepinephrine reuptake inhibitors for the treatment of tic disorders |
| DE60223718T2 (de) * | 2001-12-11 | 2008-10-30 | Eli Lilly And Co., Indianapolis | Verwendung von norepinephrin wiederaufnahmehemmern zur behandlung von kognitiven störungen |
| US6846823B2 (en) * | 2003-04-04 | 2005-01-25 | Dynogen Pharmaceuticals, Inc. | Method of treating lower urinary tract disorders |
| CA2536161A1 (en) * | 2003-08-27 | 2005-03-10 | Eli Lilly And Company | Treatment of pervasive developmental disorders with norepinephrine reuptake inhibitors |
| CN1889940A (zh) * | 2003-12-12 | 2007-01-03 | 伊莱利利公司 | 热潮红、冲动控制障碍和全身性医学病症引起的人格变化的治疗 |
| ITMI20061987A1 (it) * | 2006-10-16 | 2008-04-17 | Archimica Srl | Processo per la sintesi di arilossipropilammine ed eteroarilossipropilammine. |
| JP2020536941A (ja) * | 2017-10-16 | 2020-12-17 | エステベ ファーマシューティカルズ, ソシエダッド アノニマEsteve Pharmaceuticals, S.A. | 疼痛及び疼痛に関連する状態を治療するためのプロパンアミン誘導体 |
| CN113121394B (zh) * | 2019-12-30 | 2022-11-08 | 中国药科大学 | 一种苯氧乙酸类衍生物的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313896A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Aryloxyphenylpropylamines |
| US4626549A (en) * | 1974-01-10 | 1986-12-02 | Eli Lilly And Company | Treatment of obesity with aryloxyphenylpropylamines |
| US4018895A (en) * | 1974-01-10 | 1977-04-19 | Eli Lilly And Company | Aryloxyphenylpropylamines in treating depression |
| US4194009A (en) * | 1974-01-10 | 1980-03-18 | Eli Lilly And Company | Aryloxyphenylpropylamines for obtaining a psychotropic effect |
| US4584404A (en) * | 1974-01-10 | 1986-04-22 | Eli Lilly And Company | Substituted phenoxyphenylproply dimethylamines |
| ZA892517B (en) * | 1988-04-08 | 1990-12-28 | Lilly Co Eli | Propanamine derivatives |
-
1991
- 1991-09-27 US US07/766,993 patent/US5281624A/en not_active Expired - Lifetime
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1992
- 1992-09-22 ZA ZA927240A patent/ZA927240B/xx unknown
- 1992-09-22 SK SK2908-92A patent/SK290892A3/sk unknown
- 1992-09-22 CZ CS922908A patent/CZ281817B6/cs not_active IP Right Cessation
- 1992-09-23 MY MYPI92001704A patent/MY108304A/en unknown
- 1992-09-23 NZ NZ244460A patent/NZ244460A/en unknown
- 1992-09-24 NO NO923710A patent/NO178109C/no unknown
- 1992-09-24 DE DE69203424T patent/DE69203424T2/de not_active Expired - Fee Related
- 1992-09-24 AT AT92308709T patent/ATE124934T1/de not_active IP Right Cessation
- 1992-09-24 IL IL103277A patent/IL103277A/xx not_active IP Right Cessation
- 1992-09-24 HU HU9203051A patent/HU215519B/hu not_active IP Right Cessation
- 1992-09-24 EP EP19920308708 patent/EP0534756A3/en not_active Withdrawn
- 1992-09-24 MX MX9205433A patent/MX9205433A/es not_active IP Right Cessation
- 1992-09-25 BR BR929203743A patent/BR9203743A/pt not_active Application Discontinuation
- 1992-09-25 JP JP25632792A patent/JP3256291B2/ja not_active Expired - Fee Related
- 1992-09-25 YU YU87192A patent/YU87192A/sh unknown
- 1992-09-25 AU AU25370/92A patent/AU655075B2/en not_active Ceased
- 1992-09-25 RU SU5052706/04A patent/RU2057120C1/ru not_active IP Right Cessation
- 1992-09-25 CA CA002079162A patent/CA2079162A1/en not_active Abandoned
- 1992-09-25 FI FI924305A patent/FI111250B/fi active
- 1992-09-25 JP JP4256333A patent/JPH05238996A/ja not_active Withdrawn
- 1992-09-25 KR KR1019920017511A patent/KR100221180B1/ko not_active Expired - Fee Related
- 1992-09-25 CA CA002079161A patent/CA2079161C/en not_active Expired - Fee Related
- 1992-09-26 CN CN92111081A patent/CN1033580C/zh not_active Expired - Fee Related
- 1992-11-10 TW TW081108988A patent/TW249225B/zh active
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1997
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |