OA13359A - 1,3-dioxane derivatives and analogues thereof useful in the treatment of i.a. obesity and diabetes. - Google Patents

1,3-dioxane derivatives and analogues thereof useful in the treatment of i.a. obesity and diabetes. Download PDF

Info

Publication number: OA13359A
Authority: OA; OAPI
Prior art keywords: methyl; dioxane; carboxylate; butyl; propyl
Prior art date: 2004-01-09

Application number

OA1200600225A

Other languages

English (en)

Inventor

Vidya Bhushan Lohray

Braj Bhushan Lohray

Original Assignee

Cadila Healthcare Ltd

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.)

2004-01-09

Filing date

2005-01-07

Publication date

2007-04-13

2005-01-07 Application filed by Cadila Healthcare Ltd filed Critical Cadila Healthcare Ltd

2007-04-13 Publication of OA13359A publication Critical patent/OA13359A/en

Links

208000008589 Obesity Diseases 0.000 title claims description 10
235000020824 obesity Nutrition 0.000 title claims description 10
238000011282 treatment Methods 0.000 title description 11
206010012601 diabetes mellitus Diseases 0.000 title description 3
150000000093 1,3-dioxanes Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 71
-1 nitro, amino Chemical group 0.000 claims description 125
150000003839 salts Chemical class 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 19
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 12
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125000001424 substituent group Chemical group 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
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208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
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208000024172 Cardiovascular disease Diseases 0.000 claims description 5
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125000001769 aryl amino group Chemical group 0.000 claims description 5
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125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
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201000001421 hyperglycemia Diseases 0.000 claims description 5
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 5
229940039781 leptin Drugs 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000000033 alkoxyamino group Chemical group 0.000 claims description 4
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125000004104 aryloxy group Chemical group 0.000 claims description 4
150000001602 bicycloalkyls Chemical group 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
230000001771 impaired effect Effects 0.000 claims description 4
208000032928 Dyslipidaemia Diseases 0.000 claims description 3
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125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
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125000005110 aryl thio group Chemical group 0.000 claims description 3
208000029078 coronary artery disease Diseases 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
208000002249 Diabetes Complications Diseases 0.000 claims description 2
206010012655 Diabetic complications Diseases 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
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125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
MGPFTYCEVBVOOM-UHFFFAOYSA-N methyl 5-[4-(2,3-dihydro-1,4-benzothiazin-4-yl)butyl]-2-methyl-1,3-dioxane-2-carboxylate Chemical compound C1OC(C(=O)OC)(C)OCC1CCCCN1C2=CC=CC=C2SCC1 MGPFTYCEVBVOOM-UHFFFAOYSA-N 0.000 claims 1
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract description 14
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract description 14
239000000203 mixture Substances 0.000 abstract description 14
239000003446 ligand Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
150000003254 radicals Chemical class 0.000 description 30
239000000243 solution Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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235000019439 ethyl acetate Nutrition 0.000 description 11
125000000623 heterocyclic group Chemical group 0.000 description 11
238000000034 method Methods 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
125000003277 amino group Chemical group 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
230000000694 effects Effects 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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239000002585 base Substances 0.000 description 6
239000012267 brine Substances 0.000 description 6
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238000012360 testing method Methods 0.000 description 6
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235000011152 sodium sulphate Nutrition 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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
- A61P3/06—Antihyperlipidemics
- 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
- 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
- A61P9/10—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
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (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)
Public Health (AREA)
Diabetes (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA1200600225A 2004-01-09 2005-01-07 1,3-dioxane derivatives and analogues thereof useful in the treatment of i.a. obesity and diabetes. OA13359A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IN23MU2004		2004-01-09

Publications (1)

Publication Number	Publication Date
OA13359A true OA13359A (en)	2007-04-13

Family

ID=34856875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200600225A OA13359A (en)	2004-01-09	2005-01-07	1,3-dioxane derivatives and analogues thereof useful in the treatment of i.a. obesity and diabetes.

Country Status (14)

Country	Link
US (1)	US20070105847A1 (pt)
EP (1)	EP1709035A1 (pt)
JP (1)	JP2007517862A (pt)
CN (1)	CN1930152A (pt)
AP (1)	AP2006003688A0 (pt)
AU (1)	AU2005213545B2 (pt)
BR (1)	BRPI0506477A (pt)
CA (1)	CA2555817A1 (pt)
EA (1)	EA200601295A1 (pt)
IL (1)	IL176758A0 (pt)
NO (1)	NO20063576L (pt)
OA (1)	OA13359A (pt)
WO (1)	WO2005077943A1 (pt)
ZA (1)	ZA200605731B (pt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007096261A2 (en) *	2006-02-21	2007-08-30	F. Hoffmann-La Roche Ag	Process for the preparation of dioxane derivatives
CA2633440C (en) *	2006-02-27	2011-06-21	Cadila Healthcare Limited	1,3-dioxane carboxylic acids
EP2150111B1 (en)	2007-01-18	2016-10-19	Evolva SA	Substituted 1,3-dioxanes useful as ppar modulators
MX2009007667A (es)	2007-01-18	2011-12-08	Evolva Sa	Profarmacos de 1,3-dioxanos sustituidos y sus usos.
AR085872A1 (es)	2011-04-08	2013-10-30	Basf Se	Derivados heterobiciclicos n-sustituidos utiles para combatir parasitos en plantas y/o animales, composiciones que los contienen y metodos para combatir dichas plagas
IN2014CN00712A (pt)	2011-07-15	2015-04-03	Basf Se
IN2014CN01136A (pt)	2011-08-12	2015-04-10	Basf Se
WO2013079601A1 (en)	2011-12-02	2013-06-06	Basf Se	Method and system for monitoring crops and/or infestation of crops with harmful organismus during storage
WO2013079600A1 (en)	2011-12-02	2013-06-06	Basf Se	Method and system for monitoring crops during storage
WO2013092868A1 (en)	2011-12-21	2013-06-27	Basf Se	N-thio-anthranilamide compounds and their use as pesticides
US9732051B2 (en)	2011-12-23	2017-08-15	Basf Se	Isothiazoline compounds for combating invertebrate pests
WO2013113789A1 (en)	2012-02-02	2013-08-08	Basf Se	N-thio-anthranilamide compounds and their use as pesticides
WO2013144228A1 (en)	2012-03-29	2013-10-03	Basf Se	Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests
BR112014027133A2 (pt)	2012-05-09	2017-06-27	Basf Se	compostos, composição agrícola ou veterinária, método para o controle das pragas de invertebrados, material de propagação dos vegetais e método para o tratamento ou proteção de um animal.
KR20150100808A (ko)	2012-12-21	2015-09-02	바스프 에스이	무척추동물 해충의 방제를 위한 시클로클라빈 및 이의 유도체
WO2014128136A1 (en)	2013-02-20	2014-08-28	Basf Se	Anthranilamide compounds and their use as pesticides
CN112370455A (zh) *	2020-10-19	2021-02-19	济南大学	一种磺酰胺衍生物作为α-葡萄糖苷酶抑制剂及其应用
CN114315802B (zh) *	2021-12-14	2023-06-16	西安医学院	一种喹唑啉含氮杂环衍生物及制备方法和用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2781222A1 (fr) *	1998-07-17	2000-01-21	Lipha	Composes cycliques utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procede de preparation
IL152979A0 (en) *	2000-05-26	2003-06-24	Nippon Shinyaku Co Ltd	Heterocyclic compounds

2005
- 2005-01-07 EP EP05726428A patent/EP1709035A1/en not_active Withdrawn
- 2005-01-07 EA EA200601295A patent/EA200601295A1/ru unknown
- 2005-01-07 CA CA002555817A patent/CA2555817A1/en not_active Abandoned
- 2005-01-07 CN CNA2005800071504A patent/CN1930152A/zh active Pending
- 2005-01-07 AU AU2005213545A patent/AU2005213545B2/en not_active Ceased
- 2005-01-07 WO PCT/IN2005/000011 patent/WO2005077943A1/en not_active Ceased
- 2005-01-07 BR BRPI0506477-5A patent/BRPI0506477A/pt not_active IP Right Cessation
- 2005-01-07 US US10/585,422 patent/US20070105847A1/en not_active Abandoned
- 2005-01-07 OA OA1200600225A patent/OA13359A/en unknown
- 2005-01-07 JP JP2006548588A patent/JP2007517862A/ja not_active Withdrawn
- 2005-01-07 AP AP2006003688A patent/AP2006003688A0/xx unknown
2006
- 2006-07-09 IL IL176758A patent/IL176758A0/en unknown
- 2006-07-10 ZA ZA200605731A patent/ZA200605731B/en unknown
- 2006-08-07 NO NO20063576A patent/NO20063576L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1930152A (zh)	2007-03-14
NO20063576L (no)	2006-10-06
AU2005213545A1 (en)	2005-08-25
BRPI0506477A (pt)	2007-02-06
ZA200605731B (en)	2007-11-28
US20070105847A1 (en)	2007-05-10
WO2005077943A1 (en)	2005-08-25
CA2555817A1 (en)	2005-08-25
EA200601295A1 (ru)	2006-12-29
JP2007517862A (ja)	2007-07-05
AP2006003688A0 (en)	2006-08-31
EP1709035A1 (en)	2006-10-11
AU2005213545B2 (en)	2008-06-26
IL176758A0 (en)	2006-10-31

Publication	Publication Date	Title
AU2005213545B2 (en)	2008-06-26	1 , 3 - Dioxane derivatives and analogues thereof useful in the treatment of I.A. obesity and diabetes
CA2633440C (en)	2011-06-21	1,3-dioxane carboxylic acids
EA006858B1 (ru)	2006-04-28	Новые пирролы, обладающие гиполипидемической и гипохолестеринемической активностью, способ их получения и содержащие их фармацевтические композиции и их применение в медицине
AU2010313068A1 (en)	2012-04-26	Compounds for the treatment of dyslipidemia and related diseases
EP1445258A1 (en)	2004-08-11	Activator for peroxisome proliferator-activated receptor delta
US8742117B2 (en)	2014-06-03	Oxime derivatives
EP3083587B1 (en)	2018-04-04	Oximino derivatives for the treatment of dyslipidemia
WO2014192023A1 (en)	2014-12-04	Novel compounds suitable for the treatment of dyslipidemia
WO2005049589A2 (en)	2005-06-02	Heterocyclic compounds for the treatment of hyperlipidemia, diabetes, obesity and similar diseases
US20090012069A1 (en)	2009-01-08	Novel Antidiabetic Compounds
US20090192191A1 (en)	2009-07-30	Substituted hydroxamic acid derivatives as tnf inhibitors
MXPA06007847A (en)	2006-12-13	1 , 3 - dioxane derivatives and analogues thereof useful in the treatment of i.a. obesity and diabetes
US5478843A (en)	1995-12-26	Thiazole derivatives
AU2003302111A1 (en)	2004-06-15	Substituted aralkyl derivatives
MX2008008670A (en)	2008-09-26	1,3-dioxane carboxylic acids