UA77462C2 - Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use - Google Patents

Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use Download PDF

Info

Publication number: UA77462C2
Authority: UA; Ukraine
Prior art keywords: methoxy; morpholin; isonicotinamide; ylbenzothiazol; lower alkyl
Prior art date: 2001-11-19

Application number

UA20040604552A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Hoffmann La Roche

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.)

2001-11-19

Filing date

2002-11-11

Publication date

2006-12-15

2002-11-11 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2006-12-15 Publication of UA77462C2 publication Critical patent/UA77462C2/uk

Links

238000004519 manufacturing process Methods 0.000 title claims description 10
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical class CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims description 4
239000008177 pharmaceutical agent Substances 0.000 title 1
-1 or is acetidinyl Chemical group 0.000 claims abstract description 269
150000001875 compounds Chemical class 0.000 claims abstract description 206
125000000217 alkyl group Chemical group 0.000 claims abstract description 173
125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 22
108050000203 Adenosine receptors Proteins 0.000 claims abstract description 20
102000009346 Adenosine receptors Human genes 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 13
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 9
201000010099 disease Diseases 0.000 claims abstract description 8
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 26
239000011570 nicotinamide Substances 0.000 claims description 20
229960003966 nicotinamide Drugs 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229940126601 medicinal product Drugs 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
GUPNYUPGXQRCBK-UHFFFAOYSA-N 2-methoxy-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(C=3C(=CC=NC=3OC)C(N)=O)=NC=2C(OC)=CC=C1N1CCOCC1 GUPNYUPGXQRCBK-UHFFFAOYSA-N 0.000 claims description 3
NOXLHSPLCBIZCO-UHFFFAOYSA-N 3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-morpholin-4-ylethoxy)pyridine-4-carboxamide Chemical compound COC1=CC=C(C2=C1N=C(S2)C1=C(C(=O)N)C=CN=C1OCCN1CCOCC1)N1CCOCC1 NOXLHSPLCBIZCO-UHFFFAOYSA-N 0.000 claims description 3
BYYRQHYIVRESLW-UHFFFAOYSA-N 3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(4-methyl-3-oxopiperazin-1-yl)pyridine-4-carboxamide Chemical compound C1=2SC(C=3C(=NC=CC=3C(N)=O)N3CC(=O)N(C)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 BYYRQHYIVRESLW-UHFFFAOYSA-N 0.000 claims description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 2
VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 2
KZGJMKPUSWSYIP-UHFFFAOYSA-N 2-(3-methoxyazetidin-1-yl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1C(OC)CN1C1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 KZGJMKPUSWSYIP-UHFFFAOYSA-N 0.000 claims 1
GWSRFTFDSCYSPL-UHFFFAOYSA-N 2-methoxy-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OC)=CC(C(=O)NC=2SC3=C(C=4C=CC=CC=4)C=CC(OC)=C3N=2)=C1 GWSRFTFDSCYSPL-UHFFFAOYSA-N 0.000 claims 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
102000005962 receptors Human genes 0.000 abstract description 22
108020003175 receptors Proteins 0.000 abstract description 22
239000003446 ligand Substances 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 abstract description 3
101150051188 Adora2a gene Proteins 0.000 abstract 1
241000282414 Homo sapiens Species 0.000 description 100
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 47
229910000024 caesium carbonate Inorganic materials 0.000 description 47
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 39
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 27
239000012312 sodium hydride Substances 0.000 description 27
229910000104 sodium hydride Inorganic materials 0.000 description 27
239000000243 solution Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
239000013078 crystal Substances 0.000 description 22
239000002126 C01EB10 - Adenosine Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
229960005305 adenosine Drugs 0.000 description 20
239000007787 solid Substances 0.000 description 18
238000003756 stirring Methods 0.000 description 16
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239000012074 organic phase Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
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239000002585 base Substances 0.000 description 8
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
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235000011152 sodium sulphate Nutrition 0.000 description 8
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208000018737 Parkinson disease Diseases 0.000 description 6
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239000003054 catalyst Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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238000001665 trituration Methods 0.000 description 6
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KCELTDZFDHPTBI-UHFFFAOYSA-N 2-bromopyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(Br)=C1 KCELTDZFDHPTBI-UHFFFAOYSA-N 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Neurology (AREA)
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Psychiatry (AREA)
Addiction (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Rheumatology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

UA20040604552A 2001-11-19 2002-11-11 Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use UA77462C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01127312		2001-11-19
PCT/EP2002/012562 WO2003043636A1 (en)	2001-11-19	2002-11-11	Nicotin-or isonicotin benzothiazole derivatives

Publications (1)

Publication Number	Publication Date
UA77462C2 true UA77462C2 (en)	2006-12-15

Family

ID=8179263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040604552A UA77462C2 (en)	2001-11-19	2002-11-11	Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use

Country Status (38)

Country	Link
US (1)	US6620811B2 (no)
EP (1)	EP1448198B1 (no)
JP (1)	JP4226474B2 (no)
KR (1)	KR100577110B1 (no)
CN (1)	CN100546580C (no)
AR (1)	AR039367A1 (no)
AT (1)	ATE376831T1 (no)
AU (1)	AU2002351955B2 (no)
BR (1)	BR0214245A (no)
CA (1)	CA2467552C (no)
DE (1)	DE60223278T2 (no)
DK (1)	DK1448198T3 (no)
EA (1)	EA007502B1 (no)
EC (1)	ECSP045109A (no)
ES (1)	ES2294187T3 (no)
GT (1)	GT200200232A (no)
HR (1)	HRP20040396A2 (no)
HU (1)	HUP0402161A3 (no)
IL (2)	IL161623A0 (no)
JO (1)	JO2290B1 (no)
MA (1)	MA27083A1 (no)
MX (1)	MXPA04004684A (no)
MY (1)	MY126176A (no)
NO (1)	NO20042576L (no)
NZ (1)	NZ532802A (no)
PA (1)	PA8558001A1 (no)
PE (1)	PE20030713A1 (no)
PL (1)	PL369517A1 (no)
PT (1)	PT1448198E (no)
RS (1)	RS39904A (no)
RU (1)	RU2294933C2 (no)
SI (1)	SI1448198T1 (no)
TN (1)	TNSN04087A1 (no)
TW (1)	TW200407134A (no)
UA (1)	UA77462C2 (no)
UY (1)	UY27542A1 (no)
WO (1)	WO2003043636A1 (no)
ZA (1)	ZA200403817B (no)

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BRPI0414266A (pt) *	2003-09-19	2006-11-07	Hoffmann La Roche	derivados de tiazolopiridina como ligandos receptores da adenosina
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CA2551611C (en)	2003-12-26	2013-06-25	Kyowa Kirin Co., Ltd.	Thiazole derivatives for treating or preventing parkinson's disease
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EP1773795A1 (en) *	2004-07-22	2007-04-18	F.Hoffmann-La Roche Ag	Substituted benzothiazoles
CN1989139B (zh) *	2004-07-22	2010-05-12	弗·哈夫曼-拉罗切有限公司	苯并噻唑衍生物
KR100823799B1 (ko) *	2004-07-22	2008-04-21	에프. 호프만-라 로슈 아게	벤조티아졸 유도체
EP1807085B1 (en) *	2004-09-20	2013-08-21	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors
CA2580762A1 (en) *	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as therapeutic agents
AU2005286648A1 (en) *	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors
CA2580857A1 (en) *	2004-09-20	2006-09-28	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors
EP1827438B2 (en) †	2004-09-20	2014-12-10	Xenon Pharmaceuticals Inc.	Piperazin derivatives for inhibiting human stearoyl-coa-desaturase
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EP2289510A1 (en)	2004-09-20	2011-03-02	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes
JP5080256B2 (ja) *	2004-09-20	2012-11-21	ゼノン・ファーマシューティカルズ・インコーポレイテッド	二環式複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼ（ＳＣＤ）のインヒビターとしてのそれらの使用
JP4633123B2 (ja) *	2004-11-05	2011-02-16	エフ．ホフマン−ラロシュアーゲー	イソニコチン酸誘導体の製造方法
ES2400287T3 (es) *	2005-03-14	2013-04-08	High Point Pharmaceuticals, Llc	Derivados de benzazol, composiciones y procedimientos de uso como inhibidores de beta-secretasa
AU2006343359A1 (en) *	2005-06-03	2007-11-15	Xenon Pharmaceuticals Inc.	Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors
MX2009004314A (es) *	2006-11-13	2009-05-05	Pfizer Prod Inc	Diaril, dipiridinil y arilpiridinilderivados y usos de los mismos.
WO2010126743A1 (en)	2009-04-27	2010-11-04	High Point Pharmaceuticals, Llc	SUBSTITUTED ISOQUINOLINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE AS β-SECRETASE INHIBITORS
TWI548411B (zh)	2009-04-28	2016-09-11	Kyowa Hakko Kirin Co Ltd	Exercise disorder treatment
UA110097C2 (uk)	2009-09-02	2015-11-25		Терапевтичний агент для лікування розладів настрою
UA113383C2 (xx)	2009-09-02	2017-01-25		Терапевтичний агент для лікування тривожних розладів
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JP5248585B2 (ja) *	2010-12-15	2013-07-31	ゼノン・ファーマシューティカルズ・インコーポレイテッド	治療薬としてのニコチンアミド誘導体およびそれらの使用
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2002
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- 2002-11-11 CA CA2467552A patent/CA2467552C/en not_active Expired - Fee Related
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- 2002-11-11 RS YU39904A patent/RS39904A/sr unknown
- 2002-11-11 UA UA20040604552A patent/UA77462C2/uk unknown
- 2002-11-11 IL IL16162302A patent/IL161623A0/xx unknown
- 2002-11-11 ES ES02787632T patent/ES2294187T3/es not_active Expired - Lifetime
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2004
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- 2004-05-18 MA MA27681A patent/MA27083A1/fr unknown
- 2004-06-18 NO NO20042576A patent/NO20042576L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
RU2294933C2 (ru)	2007-03-10
CN100546580C (zh)	2009-10-07
HUP0402161A2 (hu)	2005-02-28
PA8558001A1 (es)	2003-07-28
DE60223278T2 (de)	2008-08-14
ZA200403817B (en)	2005-05-23
PT1448198E (pt)	2007-12-11
IL161623A (en)	2010-11-30
MY126176A (en)	2006-09-29
JP2005522413A (ja)	2005-07-28
NZ532802A (en)	2005-07-29
CA2467552A1 (en)	2003-05-30
ATE376831T1 (de)	2007-11-15
GT200200232A (es)	2003-06-17
CN1617722A (zh)	2005-05-18
AU2002351955A1 (en)	2003-06-10
HUP0402161A3 (en)	2010-06-28
UY27542A1 (es)	2003-05-30
IL161623A0 (en)	2004-09-27
AR039367A1 (es)	2005-02-16
HRP20040396A2 (en)	2005-04-30
EP1448198B1 (en)	2007-10-31
ES2294187T3 (es)	2008-04-01
RU2004118425A (ru)	2006-01-10
DE60223278D1 (de)	2007-12-13
US6620811B2 (en)	2003-09-16
TW200407134A (en)	2004-05-16
JP4226474B2 (ja)	2009-02-18
WO2003043636A1 (en)	2003-05-30
DK1448198T3 (da)	2008-01-07
MA27083A1 (fr)	2004-12-20
AU2002351955B2 (en)	2007-03-15
RS39904A (sr)	2006-10-27
EA200400598A1 (ru)	2005-02-24
KR100577110B1 (ko)	2006-05-10
CA2467552C (en)	2011-05-24
NO20042576L (no)	2004-06-18
SI1448198T1 (sl)	2008-02-29
EP1448198A1 (en)	2004-08-25
PE20030713A1 (es)	2003-08-23
ECSP045109A (es)	2004-06-28
TNSN04087A1 (en)	2006-06-01
KR20050044535A (ko)	2005-05-12
EA007502B1 (ru)	2006-10-27
US20030134854A1 (en)	2003-07-17
MXPA04004684A (es)	2004-08-12
BR0214245A (pt)	2004-12-14
JO2290B1 (en)	2005-09-12
PL369517A1 (en)	2005-04-18

Publication	Publication Date	Title
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