IL109108A - (S)-alpha-phenyl-2-pyrideneethanamine (S)-malate its preparation and pharmaceutical compositions containing it - Google Patents

(S)-alpha-phenyl-2-pyrideneethanamine (S)-malate its preparation and pharmaceutical compositions containing it

Info

Publication number: IL109108A
Authority: IL; Israel
Prior art keywords: phenyl; malate; compound; pyridineethanamine; enantiopure
Prior art date: 1993-04-01

Application number

IL10910894A

Other languages

English (en)

Other versions

IL109108A0 (en

Original Assignee

Astra Ab

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.)

1993-04-01

Filing date

1994-03-24

Publication date

1999-01-26

1993-04-01 Priority claimed from PCT/GB1993/000689 external-priority patent/WO1993020052A1/fr

1994-03-24 Application filed by Astra Ab filed Critical Astra Ab

1994-06-24 Publication of IL109108A0 publication Critical patent/IL109108A0/xx

1999-01-26 Publication of IL109108A publication Critical patent/IL109108A/en

Links

BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 title claims description 15
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
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208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 14
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150000003839 salts Chemical class 0.000 claims description 9
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239000003085 diluting agent Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
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239000001630 malic acid Substances 0.000 claims 2
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KRCGPQRORHRZRC-SXWHKFHYSA-N (2s)-2-hydroxybutanedioic acid;(1s)-1-phenyl-2-pyridin-2-ylethanamine Chemical compound OC(=O)[C@@H](O)CC(O)=O.C([C@H](N)C=1C=CC=CC=1)C1=CC=CC=N1 KRCGPQRORHRZRC-SXWHKFHYSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 45
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238000012360 testing method Methods 0.000 description 15
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
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HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 7
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BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
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HBTJUFDETDQJNB-UHFFFAOYSA-N 2-(2-phenyl-1h-pyridin-2-yl)ethanamine Chemical compound C=1C=CC=CC=1C1(CCN)NC=CC=C1 HBTJUFDETDQJNB-UHFFFAOYSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
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YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
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QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 1
DDOQBQRIEWHWBT-UHFFFAOYSA-N 2-azaniumyl-4-phosphonobutanoate Chemical compound OC(=O)C(N)CCP(O)(O)=O DDOQBQRIEWHWBT-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL10910894A 1993-04-01 1994-03-24 (S)-alpha-phenyl-2-pyrideneethanamine (S)-malate its preparation and pharmaceutical compositions containing it IL109108A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/GB1993/000689 WO1993020052A1 (fr)	1992-04-03	1993-04-01	1-phenyl-2-(2-pyridinyl)ethylamine enantiomere pour le traitement de maladies de degenerescence du systeme nerveux
GB939320273A GB9320273D0 (en)	1993-04-01	1993-10-01	Compound useful in therapy

Publications (2)

Publication Number	Publication Date
IL109108A0 IL109108A0 (en)	1994-06-24
IL109108A true IL109108A (en)	1999-01-26

Family

ID=26302299

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10910894A IL109108A (en)	1993-04-01	1994-03-24	(S)-alpha-phenyl-2-pyrideneethanamine (S)-malate its preparation and pharmaceutical compositions containing it

Country Status (19)

Country	Link
EP (1)	EP0691957B1 (fr)
JP (1)	JP3023987B2 (fr)
CN (1)	CN1047168C (fr)
AT (1)	ATE156813T1 (fr)
AU (1)	AU682348B2 (fr)
CA (1)	CA2159478C (fr)
DE (1)	DE69404974T2 (fr)
DK (1)	DK0691957T3 (fr)
DZ (1)	DZ1765A1 (fr)
ES (1)	ES2105672T3 (fr)
FI (1)	FI109018B (fr)
GB (1)	GB9320273D0 (fr)
GR (1)	GR3025081T3 (fr)
IL (1)	IL109108A (fr)
MA (1)	MA23154A1 (fr)
NO (1)	NO304647B1 (fr)
PH (1)	PH30950A (fr)
SG (1)	SG48204A1 (fr)
WO (1)	WO1994022831A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0356035B1 (fr) *	1988-08-12	1996-03-13	Astra Aktiebolag	Arylalkyl-amines et -amides à activité anticonvulsive et neuroprotectrice
ZA942140B (en) *	1993-04-01	1994-10-03	Fisons Corp	Salt of (S)-alpha-phenyl-2-pyridineethanamine useful in therapy
SE9901340D0 (sv) *	1999-04-15	1999-04-15	Astra Pharma Prod	Novel process
SE9901338D0 (sv) *	1999-04-15	1999-04-15	Astra Pharma Prod	Novel process
DE10301650A1 (de) *	2003-01-17	2004-07-29	Johannes-Gutenberg-Universität Mainz	Medizinisch nützliche 1-Phenyl-2-aminomethylnaphthaline, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung
EP2391606A4 (fr)	2008-12-24	2012-06-13	Astrazeneca Ab	Composés d'éthanamine et leur application pour le traitement de la dépression

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3422191A (en) *	1965-01-21	1969-01-14	Synergistics Inc	Compositions and methods for tranquilization employing salts of n-morpholine ethanol
EP0356035B1 (fr) *	1988-08-12	1996-03-13	Astra Aktiebolag	Arylalkyl-amines et -amides à activité anticonvulsive et neuroprotectrice
JP2514855B2 (ja) *	1990-08-08	1996-07-10	キッセイ薬品工業株式会社	光学活性なアラニンアニリド誘導体の酸付加塩
KR100259567B1 (ko) *	1992-04-03	2000-07-01	클래스 빌헬름슨	신경변성 질환 치료용 1-페닐-2-(2-피리디닐)에틸아민 에난티오머

1993
- 1993-10-01 GB GB939320273A patent/GB9320273D0/en active Pending
1994
- 1994-03-24 IL IL10910894A patent/IL109108A/en not_active IP Right Cessation
- 1994-03-29 DK DK94911232.0T patent/DK0691957T3/da active
- 1994-03-29 WO PCT/GB1994/000651 patent/WO1994022831A1/fr not_active Ceased
- 1994-03-29 ES ES94911232T patent/ES2105672T3/es not_active Expired - Lifetime
- 1994-03-29 EP EP94911232A patent/EP0691957B1/fr not_active Expired - Lifetime
- 1994-03-29 AU AU63802/94A patent/AU682348B2/en not_active Expired
- 1994-03-29 PH PH48016A patent/PH30950A/en unknown
- 1994-03-29 SG SG1996007883A patent/SG48204A1/en unknown
- 1994-03-29 AT AT94911232T patent/ATE156813T1/de active
- 1994-03-29 JP JP6521814A patent/JP3023987B2/ja not_active Expired - Lifetime
- 1994-03-29 CA CA002159478A patent/CA2159478C/fr not_active Expired - Lifetime
- 1994-03-29 DE DE69404974T patent/DE69404974T2/de not_active Expired - Lifetime
- 1994-03-30 DZ DZ940029A patent/DZ1765A1/fr active
- 1994-04-01 CN CN94103739A patent/CN1047168C/zh not_active Expired - Lifetime
- 1994-04-01 MA MA23459A patent/MA23154A1/fr unknown
1995
- 1995-09-28 NO NO951546A patent/NO304647B1/no not_active IP Right Cessation
- 1995-09-29 FI FI954645A patent/FI109018B/fi not_active IP Right Cessation
1997
- 1997-10-17 GR GR970402722T patent/GR3025081T3/el unknown

Also Published As

Publication number	Publication date
NO953846L (no)	1995-11-21
FI954645A0 (fi)	1995-09-29
EP0691957A1 (fr)	1996-01-17
WO1994022831A1 (fr)	1994-10-13
SG48204A1 (en)	1998-04-17
MA23154A1 (fr)	1994-12-31
JP3023987B2 (ja)	2000-03-21
CA2159478A1 (fr)	1994-10-13
EP0691957B1 (fr)	1997-08-13
NO304647B1 (no)	1999-01-25
AU682348B2 (en)	1997-10-02
DK0691957T3 (da)	1997-10-27
DE69404974T2 (de)	1997-12-18
IL109108A0 (en)	1994-06-24
FI954645L (fi)	1995-11-29
ATE156813T1 (de)	1997-08-15
NO953846D0 (no)	1995-09-28
GR3025081T3 (en)	1998-01-30
CN1047168C (zh)	1999-12-08
DE69404974D1 (de)	1997-09-18
PH30950A (en)	1997-12-23
CN1098095A (zh)	1995-02-01
ES2105672T3 (es)	1997-10-16
GB9320273D0 (en)	1993-11-17
FI109018B (fi)	2002-05-15
CA2159478C (fr)	2005-01-25
AU6380294A (en)	1994-10-24
JPH08508292A (ja)	1996-09-03
DZ1765A1 (fr)	2002-02-17

Legal Events

Date	Code	Title
1999-07-14	FF	Patent granted
2000-07-26	KB	Patent renewed
2000-08-31	KB	Patent renewed
2004-05-12	KB	Patent renewed
2008-04-13	KB	Patent renewed
2012-03-29	KB	Patent renewed
2014-11-30	EXP	Patent expired

Publication	Publication Date	Title
EP0633879B1 (fr)	1998-03-11	1-phenyl-2-(2-pyridinyl)ethylamine enantiomere pour le traitement de maladies de degenerescence du systeme nerveux
EP1317426B1 (fr)	2005-11-16	Acides $g(b)-thio-amines
EP0691957B1 (fr)	1997-08-13	(s)-alpha-phenyl-2-pyridineethanamine (s)-malate et son utilisation en tant que medicament
JPH06293761A (ja)	1994-10-21	スピロ橋かけ型および非橋かけ型複素環式化合物
DE69431050T2 (de)	2003-03-13	PYRIDO[2,3-b](1,4)BENZODIAZEPINONE ALS M2-REZEPTORLIGAND ZUR BEHANDLUNG NEUROLOGISCHER STÖRUNGEN
US5455259A (en)	1995-10-03	Compounds for the treatment of neurodegenerative disorders
DE69218795T2 (de)	1997-07-10	Verbindungen,die neurotransmitter freisetzen,um die lernfähigkeit zu erhöhen
EP0691958B1 (fr)	1997-08-13	Benzoate (s)-alpha-phenyl-2-pyridineethanamine et son utilisation en tant que medicament
WO1995023135A1 (fr)	1995-08-31	Derives de diphenyl-2-piperidinone et -2-pyrrolidinone possedant une activite anticonvulsivante et neuroprotectrice
HK1009331B (en)	1999-05-28	Enantiomeric 1-phenyl-2-(2-pyridinyl) ethylamine for the treatment of neurodegenerative disorders
CA2028645A1 (fr)	1991-04-28	Utilisation d'arylalkylamides dans le traitement d'affections neurodegeneratives
TW390875B (en)	2000-05-21	(S) -<alpha>-phenyl-2-pyridineethanamine (S)-malate useful in therary, its perparing process and pharmaceutical composition comprising the same