ZA200401375B - Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluro-propanamide derivatives which elevate pyruvate dehydro-genase activity. - Google Patents

Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluro-propanamide derivatives which elevate pyruvate dehydro-genase activity. Download PDF

Info

Publication number: ZA200401375B
Authority: ZA; South Africa
Prior art keywords: formula; compound; pharmaceutically acceptable; acceptable salt; vivo hydrolysable
Prior art date: 2001-08-23

Application number

ZA200401375A

Other languages

English (en)

Inventor

Roger John Butlin

Original Assignee

Astrazeneca 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.)

2001-08-23

Filing date

2004-02-19

Publication date

2004-11-17

2004-02-19 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2004-11-17 Publication of ZA200401375B publication Critical patent/ZA200401375B/en

Links

230000000694 effects Effects 0.000 title claims description 43
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238000000034 method Methods 0.000 claims description 57
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238000001727 in vivo Methods 0.000 claims description 42
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
108091006091 regulatory enzymes Proteins 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000012536 storage buffer Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229960002363 thiamine pyrophosphate Drugs 0.000 description 1
235000008170 thiamine pyrophosphate Nutrition 0.000 description 1
239000011678 thiamine pyrophosphate Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000583 toxicological profile Toxicity 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
206010046494 urge incontinence Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Hospice & Palliative Care (AREA)
Emergency Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

ZA200401375A 2001-08-23 2004-02-19 Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluro-propanamide derivatives which elevate pyruvate dehydro-genase activity. ZA200401375B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0120471.8A GB0120471D0 (en)	2001-08-23	2001-08-23	Chemical compounds

Publications (1)

Publication Number	Publication Date
ZA200401375B true ZA200401375B (en)	2004-11-17

Family

ID=9920849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200401375A ZA200401375B (en)	2001-08-23	2004-02-19	Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluro-propanamide derivatives which elevate pyruvate dehydro-genase activity.

Country Status (23)

Country	Link
US (2)	US20050026931A1 (ar)
EP (1)	EP1425003A1 (ar)
JP (1)	JP2005506976A (ar)
KR (1)	KR20040030164A (ar)
CN (2)	CN101328157A (ar)
AR (1)	AR037497A1 (ar)
AU (1)	AU2002321520B2 (ar)
BR (1)	BR0212043A (ar)
CA (1)	CA2458121A1 (ar)
CO (1)	CO5560539A2 (ar)
GB (1)	GB0120471D0 (ar)
HU (1)	HUP0401149A2 (ar)
IL (1)	IL160455A0 (ar)
IS (1)	IS7157A (ar)
MX (1)	MXPA04001552A (ar)
NO (1)	NO326745B1 (ar)
NZ (1)	NZ531261A (ar)
PL (1)	PL368615A1 (ar)
RU (1)	RU2301805C2 (ar)
SA (1)	SA02230268B1 (ar)
UA (1)	UA77967C2 (ar)
WO (1)	WO2003017995A1 (ar)
ZA (1)	ZA200401375B (ar)

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* Cited by examiner, † Cited by third party
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KR101108196B1 (ko) *	2009-11-04	2012-01-31	(주)유로파	쓰레기 자동 집하시설의 관로 전환기
RU2693457C2 (ru) *	2013-07-18	2019-07-03	Фондацьоне Иституто Итальяно Ди Текнолоджия	Фенилкарбаматы и их применения в качестве ингибиторов фермента гидролазы амидов жирных кислот (faah) и модуляторов d3 допаминового рецептора (d3dr)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4537618A (en) *	1982-05-26	1985-08-27	Ciba Geigy Corporation	N-phenylsulfonyl-N'-pyrimidinylureas
GB9116069D0 (en) *	1991-07-25	1991-09-11	Ici Plc	Therapeutic amides
EP0539329A1 (de) *	1991-10-25	1993-04-28	Ciba-Geigy Ag	Acetylen-Verbindungen, verwendbar als Leukotrien-Antagonisten
GB9309716D0 (en) *	1993-05-12	1993-06-23	Zeneca Ltd	Heterocyclic derivatives
GB9310095D0 (en) *	1993-05-17	1993-06-30	Zeneca Ltd	Therapeutic compounds
GB9804648D0 (en) *	1998-03-06	1998-04-29	Zeneca Ltd	Chemical compounds
GB9805520D0 (en) *	1998-03-17	1998-05-13	Zeneca Ltd	Chemical compounds
GB9811427D0 (en) *	1998-05-29	1998-07-22	Zeneca Ltd	Chemical compounds
WO2001017956A1 (en) *	1999-09-04	2001-03-15	Astrazeneca Ab	Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity

2001
- 2001-08-23 GB GBGB0120471.8A patent/GB0120471D0/en not_active Ceased
2002
- 2002-08-21 CN CNA2008101259041A patent/CN101328157A/zh active Pending
- 2002-08-21 US US10/487,261 patent/US20050026931A1/en not_active Abandoned
- 2002-08-21 HU HU0401149A patent/HUP0401149A2/hu unknown
- 2002-08-21 UA UA2004032170A patent/UA77967C2/uk unknown
- 2002-08-21 BR BR0212043-7A patent/BR0212043A/pt not_active IP Right Cessation
- 2002-08-21 CA CA002458121A patent/CA2458121A1/en not_active Abandoned
- 2002-08-21 KR KR10-2004-7002620A patent/KR20040030164A/ko not_active Ceased
- 2002-08-21 IL IL16045502A patent/IL160455A0/xx unknown
- 2002-08-21 NZ NZ531261A patent/NZ531261A/en unknown
- 2002-08-21 CN CNA028207734A patent/CN1571665A/zh active Pending
- 2002-08-21 JP JP2003522515A patent/JP2005506976A/ja active Pending
- 2002-08-21 MX MXPA04001552A patent/MXPA04001552A/es not_active Application Discontinuation
- 2002-08-21 AU AU2002321520A patent/AU2002321520B2/en not_active Ceased
- 2002-08-21 PL PL02368615A patent/PL368615A1/xx not_active Application Discontinuation
- 2002-08-21 WO PCT/GB2002/003867 patent/WO2003017995A1/en not_active Ceased
- 2002-08-21 RU RU2004108466/04A patent/RU2301805C2/ru not_active IP Right Cessation
- 2002-08-21 EP EP02755224A patent/EP1425003A1/en not_active Withdrawn
- 2002-08-23 AR ARP020103172A patent/AR037497A1/es unknown
- 2002-08-26 SA SA02230268A patent/SA02230268B1/ar unknown
2004
- 2004-02-19 IS IS7157A patent/IS7157A/is unknown
- 2004-02-19 NO NO20040725A patent/NO326745B1/no not_active IP Right Cessation
- 2004-02-19 ZA ZA200401375A patent/ZA200401375B/en unknown
- 2004-03-16 CO CO04024614A patent/CO5560539A2/es not_active Application Discontinuation
2006
- 2006-11-20 US US11/601,854 patent/US20070208032A1/en not_active Abandoned

Also Published As

Publication number	Publication date
JP2005506976A (ja)	2005-03-10
KR20040030164A (ko)	2004-04-08
WO2003017995A1 (en)	2003-03-06
CO5560539A2 (es)	2005-09-30
CN101328157A (zh)	2008-12-24
US20070208032A1 (en)	2007-09-06
NO326745B1 (no)	2009-02-09
UA77967C2 (en)	2007-02-15
NO20040725L (no)	2004-02-19
EP1425003A1 (en)	2004-06-09
PL368615A1 (en)	2005-04-04
HUP0401149A2 (hu)	2004-12-28
BR0212043A (pt)	2004-08-17
AR037497A1 (es)	2004-11-17
AU2002321520B2 (en)	2008-06-12
IL160455A0 (en)	2004-07-25
RU2301805C2 (ru)	2007-06-27
US20050026931A1 (en)	2005-02-03
NZ531261A (en)	2005-09-30
CN1571665A (zh)	2005-01-26
CA2458121A1 (en)	2003-03-06
IS7157A (is)	2004-02-19
SA02230268B1 (ar)	2007-02-17
MXPA04001552A (es)	2004-05-17
GB0120471D0 (en)	2001-10-17
RU2004108466A (ru)	2005-09-20

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