CA2420694C - Guanidinobenzamides as mc4-r agonists - Google Patents

Guanidinobenzamides as mc4-r agonists Download PDF

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Publication number
CA2420694C
CA2420694C CA002420694A CA2420694A CA2420694C CA 2420694 C CA2420694 C CA 2420694C CA 002420694 A CA002420694 A CA 002420694A CA 2420694 A CA2420694 A CA 2420694A CA 2420694 C CA2420694 C CA 2420694C
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Prior art keywords
groups
substituted
unsubstituted
ethyl
group
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Expired - Fee Related
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CA002420694A
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English (en)
French (fr)
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CA2420694A1 (en
Inventor
Paul A. Renhowe
Daniel Chu
Rustum Boyce
Zhi-Jie Ni
David Duhl
Effie Tozzo
Kirk Johnson
David Myles
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Novartis Vaccines and Diagnostics Inc
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Novartis Vaccines and Diagnostics Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • 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
    • C07D307/18—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C07D309/08—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002420694A 2000-08-31 2001-08-31 Guanidinobenzamides as mc4-r agonists Expired - Fee Related CA2420694C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US23056500P 2000-08-31 2000-08-31
US60/230,565 2000-08-31
US24557900P 2000-11-06 2000-11-06
US60/245,579 2000-11-06
PCT/US2001/027206 WO2002018327A2 (en) 2000-08-31 2001-08-31 Guanidinobenzamides as mc4-r agonists

Publications (2)

Publication Number Publication Date
CA2420694A1 CA2420694A1 (en) 2002-03-07
CA2420694C true CA2420694C (en) 2009-06-23

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CA002420694A Expired - Fee Related CA2420694C (en) 2000-08-31 2001-08-31 Guanidinobenzamides as mc4-r agonists

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US (2) US6638927B2 (US07132539-20061107-C00040.png)
EP (1) EP1409468B9 (US07132539-20061107-C00040.png)
JP (1) JP4166567B2 (US07132539-20061107-C00040.png)
KR (1) KR20030034163A (US07132539-20061107-C00040.png)
CN (1) CN1659156A (US07132539-20061107-C00040.png)
AP (1) AP2003002755A0 (US07132539-20061107-C00040.png)
AT (1) ATE414067T1 (US07132539-20061107-C00040.png)
AU (2) AU8860401A (US07132539-20061107-C00040.png)
BG (1) BG107639A (US07132539-20061107-C00040.png)
BR (1) BR0113643A (US07132539-20061107-C00040.png)
CA (1) CA2420694C (US07132539-20061107-C00040.png)
CZ (1) CZ2003882A3 (US07132539-20061107-C00040.png)
DE (1) DE60136571D1 (US07132539-20061107-C00040.png)
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HU (1) HUP0302067A2 (US07132539-20061107-C00040.png)
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PL (1) PL360698A1 (US07132539-20061107-C00040.png)
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Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1385823E (pt) * 2001-04-09 2007-01-31 Novartis Vaccines & Diagnostic Compostos de guanidino como agonistas do receptor de melanocortina-4 (r-mc4)
ES2296956T5 (es) * 2001-06-11 2011-07-12 Xenoport, Inc. Profármacos de análogos de gaba, composiciones y sus usos.
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US6818787B2 (en) 2001-06-11 2004-11-16 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en) 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US20030195187A1 (en) * 2002-02-04 2003-10-16 Chiron Corporation Guanidino compounds
US20050124652A1 (en) * 2002-02-04 2005-06-09 Rustum Boyce Guanidino compounds
US20030207814A1 (en) * 2002-02-04 2003-11-06 Chiron Corporation Novel guanidinyl derivatives
JP2005524649A (ja) * 2002-02-25 2005-08-18 カイロン コーポレーション Ｍｃ４−ｒアゴニストの鼻腔内投与
ATE478867T1 (de) * 2002-05-23 2010-09-15 Novartis Vaccines & Diagnostic Substituierte quinazolinone verbindungen
US7125904B2 (en) * 2002-10-11 2006-10-24 Portela & C.A., S.A. Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation
AU2003297629A1 (en) * 2002-12-04 2004-06-23 Ore Pharmaceuticals Inc. Modulators of melanocortin receptor
ES2423800T3 (es) 2003-03-28 2013-09-24 Novartis Vaccines And Diagnostics, Inc. Uso de compuestos orgánicos para la inmunopotenciación
KR20060018217A (ko) 2003-05-23 2006-02-28 카이론 코포레이션 Ｍｃ4-ｒ 작용제로서 구아니디노-치환된 퀴나졸리논 화합물
JP2005306839A (ja) * 2003-08-29 2005-11-04 Takeda Chem Ind Ltd 二環性ピペラジン化合物およびその用途
US7795267B2 (en) 2003-08-29 2010-09-14 Takeda Pharmaceutical Company Limited Bicyclic piperazine compound having TGR23 antagonistic activity
EP1686996A4 (en) 2003-11-19 2008-11-12 Novartis Vaccines & Diagnostic QUINAZOLINONE COMPOUNDS WITH REDUCED BIOACCUMULATION
EP1734963A4 (en) 2004-04-02 2008-06-18 Merck & Co Inc METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER
US7504413B2 (en) 2004-05-06 2009-03-17 Cytokinetics, Inc. N-(4-(imidazo[1,2A]pyridin-YL)phenethyl)benzamide inhibitors of the mitotic kinesin CENP-E for treating certain cellular proliferation diseases
US7618981B2 (en) 2004-05-06 2009-11-17 Cytokinetics, Inc. Imidazopyridinyl-benzamide anti-cancer agents
US7795448B2 (en) 2004-05-06 2010-09-14 Cytokinetics, Incorporated Imidazoyl-benzamide anti-cancer agents
US8795725B2 (en) 2004-11-04 2014-08-05 Xenoport, Inc. GABA analog prodrug sustained release oral dosage forms
US20070021433A1 (en) 2005-06-03 2007-01-25 Jian-Qiang Fan Pharmacological chaperones for treating obesity
WO2007022964A2 (de) 2005-08-24 2007-03-01 Abbott Gmbh & Co. Kg Hetaryl substituierte guanidinverbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren
CN101466669B (zh) 2006-06-09 2011-11-30 阿克申制药公司 苯基吡咯氨基胍衍生物
GB0624987D0 (en) 2006-12-14 2007-01-24 Acure Pharma Ab Novel aminoguanidines as melanocortin receptor ligands
UA99555C2 (en) 2008-11-12 2012-08-27 Элджи Лайф Саенсез Лтд. Melanocortin receptor agonists
WO2010056717A1 (en) 2008-11-17 2010-05-20 Merck Sharp & Dohme Corp. Substituted bicyclic amines for the treatment of diabetes
WO2011011508A1 (en) 2009-07-23 2011-01-27 Schering Corporation Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors
WO2011011506A1 (en) 2009-07-23 2011-01-27 Schering Corporation Spirocyclic oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors
US8476227B2 (en) 2010-01-22 2013-07-02 Ethicon Endo-Surgery, Inc. Methods of activating a melanocortin-4 receptor pathway in obese subjects
US9044606B2 (en) 2010-01-22 2015-06-02 Ethicon Endo-Surgery, Inc. Methods and devices for activating brown adipose tissue using electrical energy
US8785634B2 (en) 2010-04-26 2014-07-22 Merck Sharp & Dohme Corp Spiropiperidine prolylcarboxypeptidase inhibitors
EP2568812B1 (en) 2010-05-11 2016-10-26 Merck Sharp & Dohme Corp. Novel prolylcarboxypeptidase inhibitors
US9006268B2 (en) 2010-06-11 2015-04-14 Merck Sharp & Dohme Corp. Prolylcarboxypeptidase inhibitors
US9018395B2 (en) 2011-01-27 2015-04-28 Université de Montréal Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators
US10092738B2 (en) 2014-12-29 2018-10-09 Ethicon Llc Methods and devices for inhibiting nerves when activating brown adipose tissue
US10080884B2 (en) 2014-12-29 2018-09-25 Ethicon Llc Methods and devices for activating brown adipose tissue using electrical energy
CN115850117B (zh) * 2022-11-15 2024-06-04 黎明化工研究设计院有限责任公司 一种制备1,4-环己烷二异氰酸酯的方法

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3177218A (en) * 1962-01-17 1965-04-06 Monsanto Chemicals Methylene-bis(2-guanidino-4-methylquinazoline)
DE2623846A1 (de) * 1976-05-28 1977-12-15 Hoechst Ag 4-chinazolinyl-guanidine und verfahren zu ihrer herstellung
US4287341A (en) * 1979-11-01 1981-09-01 Pfizer Inc. Alkoxy-substituted-6-chloro-quinazoline-2,4-diones
DE3270716D1 (en) * 1981-02-27 1986-05-28 Ici Plc Guanidino-substituted heterocyclic derivatives having histamine h-2 antagonist activity
DE3267110D1 (de) * 1981-05-18 1985-12-05 Ici Plc Amidine derivatives
US4921939A (en) * 1985-03-19 1990-05-01 Universite Claude Bernard -Lyon 1 Sweetening agents
JPS6229566A (ja) 1985-07-30 1987-02-07 Taiyo Yakuhin Kogyo Kk 新規グアニジノメチル安息香酸誘導体
US4948891A (en) 1988-05-24 1990-08-14 Pfizer Inc. Benzamide protease inhibitors
US4948901A (en) 1988-05-24 1990-08-14 Pfizer Inc. Benzamide protease inhibitors
US4874864A (en) 1988-05-24 1989-10-17 Pfizer Inc. Benzamide protease inhibitors
US5055479A (en) 1988-06-16 1991-10-08 Sankyo Company, Limited Method of treating cachexia
GB8926512D0 (en) 1989-11-23 1990-01-10 Pfizer Ltd Therapeutic agents
CA2032420A1 (en) 1989-12-22 1991-06-23 Akira Okuyama Guanidinobenzene derivatives
US5124328A (en) 1990-10-11 1992-06-23 Merck & Co., Inc. Morpholine derivatives compositions and use
WO1994021621A1 (en) 1993-03-23 1994-09-29 Astra Aktiebolag Guanidine derivatives useful in therapy
CZ29996A3 (en) 1993-08-12 1996-09-11 Astra Ab Amidine derivatives with activities of nitrogen oxide sythetase
US5547966A (en) 1993-10-07 1996-08-20 Bristol-Myers Squibb Company Aryl urea and related compounds
US5599984A (en) 1994-01-21 1997-02-04 The Picower Institute For Medical Research Guanylhydrazones and their use to treat inflammatory conditions
US5637439A (en) 1994-11-07 1997-06-10 Mitsubishi Paper Mills Ltd. Photographic silver halide photosensitive material and method for developing the same
AU4534596A (en) 1995-02-09 1996-08-27 Novo Nordisk A/S Compounds with growth hormone releasing properties
DE19544687A1 (de) 1995-11-30 1997-06-05 Thomae Gmbh Dr K Aminosäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE19544685A1 (de) 1995-11-30 1997-06-05 Thomae Gmbh Dr K Aminosäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
AU2536097A (en) 1996-03-29 1997-10-22 G.D. Searle & Co. Para-substituted phenylpropanoic acid derivatives as integrin antagonists
US5889025A (en) 1996-05-06 1999-03-30 Reddy's Research Foundation Antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
US6127343A (en) 1996-05-14 2000-10-03 Novo Nordisk A/S Somatostatin agonists and antagonists
DE69713402T2 (de) 1996-08-23 2002-11-07 Agouron Pharma Liganden des neuropeptids y
JP2001502712A (ja) 1996-10-31 2001-02-27 ノボ ノルディスク アクティーゼルスカブ 束縛されたソマトスタチン・アゴニスト及びアンタゴニスト
BR9713536A (pt) * 1996-11-25 2000-11-07 Procter & Gamble Compostos heterocìclicos de guanidinila úteis como agonistas de adrenoceptores alfa-2
AU2930797A (en) 1997-05-02 1997-11-19 Dr. Reddy's Research Foundation Novel antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
EP1085869A4 (en) * 1998-06-11 2001-10-04 Merck & Co Inc SPIRO PIPERID DERIVATIVES AS MELANOCORTIN RECEPTORAGONISTS
DE19831710A1 (de) * 1998-07-15 2000-01-20 Merck Patent Gmbh Diacylhydrazinderivate
FR2784678B1 (fr) 1998-09-23 2002-11-29 Sod Conseils Rech Applic Nouveaux derives de n-(iminomethyl)amines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant
US6297233B1 (en) * 1999-02-09 2001-10-02 Bristol-Myers Squibb Company Lactam inhibitors of FXa and method
WO2000074679A1 (en) 1999-06-04 2000-12-14 Merck & Co., Inc. Substituted piperidines as melanocortin-4 receptor agonists
CA2381008A1 (en) 1999-08-04 2001-02-15 Millennium Pharmaceuticals, Inc. Melanocortin-4 receptor binding compounds and methods of use thereof
GB0002059D0 (en) 2000-01-28 2000-03-22 Melacure Therapeutics Ab Novel aromatic amines
AU2001228681A1 (en) 2000-01-28 2001-08-07 Melacure Therapeutics Ab Novel aromatic amines and amides acting on the melanocortin receptors
CA2398728A1 (en) 2000-01-28 2001-08-02 Ivars Kalvins Novel melanocortin receptor agonists and antagonists
AU4929601A (en) 2000-03-23 2001-10-03 Merck & Co Inc Substituted piperidines as melanocortin receptor agonists
AU4928101A (en) 2000-03-23 2001-10-03 Merck & Co Inc Spiropiperidine derivatives as melanocortin receptor agonists
GB0102668D0 (en) 2001-02-02 2001-03-21 Glaxo Group Ltd Compounds
PT1385823E (pt) * 2001-04-09 2007-01-31 Novartis Vaccines & Diagnostic Compostos de guanidino como agonistas do receptor de melanocortina-4 (r-mc4)
ATE478867T1 (de) 2002-05-23 2010-09-15 Novartis Vaccines & Diagnostic Substituierte quinazolinone verbindungen

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