CA2168097A1 - Substituted 2-aminotetralins - Google Patents

Substituted 2-aminotetralins

Info

Publication number
CA2168097A1
CA2168097A1 CA002168097A CA2168097A CA2168097A1 CA 2168097 A1 CA2168097 A1 CA 2168097A1 CA 002168097 A CA002168097 A CA 002168097A CA 2168097 A CA2168097 A CA 2168097A CA 2168097 A1 CA2168097 A1 CA 2168097A1
Authority
CA
Canada
Prior art keywords
aminotetralins
substituted
hyperprolactinemia
parkinsonism
glaucoma
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.)
Granted
Application number
CA002168097A
Other languages
French (fr)
Other versions
CA2168097C (en
Inventor
Mark C. Sleevi
Gevork Minaskanian
L. Meredith Moses
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.)
Aderis Pharmaceuticals Inc
Original Assignee
Mark C. Sleevi
Gevork Minaskanian
L. Meredith Moses
Whitby Research, Inc.
Discovery Therapeutics, Inc.
Aderis Pharmaceuticals, 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.)
Filing date
Publication date
Application filed by Mark C. Sleevi, Gevork Minaskanian, L. Meredith Moses, Whitby Research, Inc., Discovery Therapeutics, Inc., Aderis Pharmaceuticals, Inc. filed Critical Mark C. Sleevi
Publication of CA2168097A1 publication Critical patent/CA2168097A1/en
Application granted granted Critical
Publication of CA2168097C publication Critical patent/CA2168097C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen 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 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C217/04—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 acyclic and saturated
    • C07C217/06—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 acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—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 acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C217/04—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 acyclic and saturated
    • C07C217/06—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 acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/12—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 acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen 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
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen 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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen 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 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Abstract

Optically active or racemic compounds represented by formula (1] wherein R1, R2, R3, R5 and n are defined as in the specification, and pharmaceutically ac-ceptable salts thereof. These compounds are useful for alleviating Parkinsonism, glaucoma, hyperprolactinemia and for inducing weight loss in mammals.
CA002168097A 1993-08-05 1994-08-05 Substituted 2-aminotetralins Expired - Fee Related CA2168097C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/102,436 US5382596A (en) 1993-08-05 1993-08-05 Substituted 2-aminotetralins
US08/102,436 1993-08-05
PCT/US1994/008845 WO1995004532A1 (en) 1993-08-05 1994-08-05 Substituted 2-aminotetralins

Publications (2)

Publication Number Publication Date
CA2168097A1 true CA2168097A1 (en) 1995-02-16
CA2168097C CA2168097C (en) 2005-06-28

Family

ID=22289833

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002168097A Expired - Fee Related CA2168097C (en) 1993-08-05 1994-08-05 Substituted 2-aminotetralins

Country Status (11)

Country Link
US (1) US5382596A (en)
EP (1) EP0717620B1 (en)
JP (1) JP3839043B2 (en)
AT (1) ATE207745T1 (en)
AU (1) AU682388B2 (en)
CA (1) CA2168097C (en)
DE (1) DE69428903T2 (en)
DK (1) DK0717620T3 (en)
ES (1) ES2166379T3 (en)
PT (1) PT717620E (en)
WO (1) WO1995004532A1 (en)

Families Citing this family (30)

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US5646188A (en) * 1995-07-05 1997-07-08 Teva Pharmaceutical Industries, Ltd. Polyamine derivatives of 1-aminoindan
DE19814084B4 (en) * 1998-03-30 2005-12-22 Lts Lohmann Therapie-Systeme Ag D2 agonist-containing transdermal therapeutic system for the treatment of Parkinson's syndrome and process for its preparation
US6372920B1 (en) 1999-11-23 2002-04-16 Aderis Pharmaceuticals, Inc. Process for preparing nitrogen-substituted aminotetralins
DE10041479A1 (en) * 2000-08-24 2002-03-14 Sanol Arznei Schwarz Gmbh New pharmaceutical composition for the administration of N-0923
DE10041478A1 (en) * 2000-08-24 2002-03-14 Sanol Arznei Schwarz Gmbh New pharmaceutical composition
US20030027793A1 (en) * 2001-05-08 2003-02-06 Thomas Lauterback Transdermal treatment of parkinson's disease
US20030026830A1 (en) * 2001-05-08 2003-02-06 Thomas Lauterback Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine
US20040048779A1 (en) * 2002-05-06 2004-03-11 Erwin Schollmayer Use of rotigotine for treating the restless leg syndrome
DE10234673B4 (en) * 2002-07-30 2007-08-16 Schwarz Pharma Ag Hot-melt TTS for the administration of rotigotine and process for its preparation, and use of rotigotine in the manufacture of a hot-melt TTS
US8246980B2 (en) * 2002-07-30 2012-08-21 Ucb Pharma Gmbh Transdermal delivery system
US8211462B2 (en) * 2002-07-30 2012-07-03 Ucb Pharma Gmbh Hot-melt TTS for administering rotigotine
US8246979B2 (en) * 2002-07-30 2012-08-21 Ucb Pharma Gmbh Transdermal delivery system for the administration of rotigotine
DE60204229T2 (en) * 2002-12-02 2006-02-02 Schwarz Pharma Ag Administration of rotigotine for the treatment of Parkinson's disease by iontophoresis
DE10261696A1 (en) 2002-12-30 2004-07-15 Schwarz Pharma Ag Device for the transdermal administration of rotigotine base
BRPI0409492A (en) * 2003-04-18 2006-05-02 Pharmacia & Up John Company Ll combination therapies
DE10334188B4 (en) * 2003-07-26 2007-07-05 Schwarz Pharma Ag Use of rotigotine to treat depression
DE10359528A1 (en) * 2003-12-18 2005-07-28 Schwarz Pharma Ag (S) -2-N-propylamino-5-hydroxytetralin as a D3 agonist therapeutic
DE10361258A1 (en) * 2003-12-24 2005-07-28 Schwarz Pharma Ag Use of substituted 2-aminotetralins for the preventive treatment of Parkinson's disease
US20050197385A1 (en) * 2004-02-20 2005-09-08 Schwarz Pharma Ag Use of rotigotine for treatment or prevention of dopaminergic neuron loss
DE102004014841B4 (en) * 2004-03-24 2006-07-06 Schwarz Pharma Ag Use of rotigotine for the treatment and prevention of Parkinson-Plus syndrome
TWI392670B (en) * 2006-06-22 2013-04-11 Ucb Pharma Gmbh Use of substituted 2-aminotetralines for the manufacture of a medicament for the prevention, alleviation and/or treatment of various types of pain
EP1987815A1 (en) * 2007-05-04 2008-11-05 Schwarz Pharma Ag Oronasopharyngeally deliverable pharmaceutical compositions of dopamine agonists for the prevention and/or treatment of restless limb disorders
US8592477B2 (en) * 2007-11-28 2013-11-26 Ucb Pharma Gmbh Polymorphic form of rotigotine and process for production
IT1392387B1 (en) * 2008-09-26 2012-03-02 Solmag S P A Ora Fidia Farmaceutici S P A PROCESS FOR ROTIGOTINE PREPARATION
EP2281559A1 (en) 2009-06-26 2011-02-09 UCB Pharma GmbH Pharmaceutical composition comprising rotigotine salts (acid or Na), especially for iontophoresis
CN102010400B (en) 2009-09-07 2015-02-04 药源药物化学（上海）有限公司 S-5-substituted-N-2'-(thiofuran-2-yl-) ethyl-1,2,3,4-tetranap-2-amine or chiral hydrochloric acid and application thereof to preparation of rotigotine
SI2515887T1 (en) 2009-12-22 2018-10-30 Ucb Biopharma Sprl Polyvinylpyrrolidone for the stabilization of a solid dispersion of the non-crystalline form of rotigotine
AU2011268871C1 (en) 2010-06-25 2015-06-04 Ucb Pharma Gmbh Processes for the resolution of nitrogen substituted (S) - 5 -alkoxy- 2 -aminotetralin derivatives
EP2723727B1 (en) 2011-06-27 2017-03-01 Shan Dong Luye Pharmaceutical Co., Ltd. Method for industrially preparing nitrogen substituted amino-5,6,7,8-tetrahydronaphthol
CN114890978B (en) * 2022-04-19 2023-07-25 宿迁医美科技有限公司 Phenolic compound, and preparation method and application thereof

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NL298071A (en) * 1963-06-04
US3991207A (en) * 1971-03-18 1976-11-09 Pfizer Inc. Combination therapy for Parkinson's disease
CA1017359A (en) * 1972-07-03 1977-09-13 Frederic P. Hauck Substituted cyclic polymethylene phenols
US3930022A (en) * 1972-07-03 1975-12-30 Squibb & Sons Inc Certain tetrahydronaphthalenes used in the treatment of cardiac arrhythmia
US4267373A (en) * 1972-07-03 1981-05-12 E. R. Squibb & Sons, Inc. 5,6,7,8-Tetrahydronaphthalene hypotensive agents
US4057582A (en) * 1973-09-26 1977-11-08 Abbott Laboratories Aminotetralins and use in inducing anesthesia
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DK254975A (en) * 1974-06-12 1975-12-13 Takeda Chemical Industries Ltd METHOD OF PREPARATION OF AMINOTETRALOL COMPOUNDS
EP0026848B1 (en) * 1979-09-14 1983-05-04 Sandoz Ag Derivatives of tetraline, their preparation and medicaments containing these compounds
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CA2065450A1 (en) * 1989-07-05 1991-01-06 James V. Peck Substituted 2-aminotetralins

Also Published As

Publication number Publication date
EP0717620B1 (en) 2001-10-31
CA2168097C (en) 2005-06-28
JP3839043B2 (en) 2006-11-01
ES2166379T3 (en) 2002-04-16
US5382596A (en) 1995-01-17
AU7520794A (en) 1995-02-28
DE69428903D1 (en) 2001-12-06
PT717620E (en) 2002-04-29
ATE207745T1 (en) 2001-11-15
EP0717620A4 (en) 1997-05-28
WO1995004532A1 (en) 1995-02-16
DK0717620T3 (en) 2001-11-26
JPH09501434A (en) 1997-02-10
DE69428903T2 (en) 2002-04-04
AU682388B2 (en) 1997-10-02
EP0717620A1 (en) 1996-06-26

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Effective date: 20140805