AU2004238258A1 - Preparation and use of aryl alkyl acid derivatives for the treatment of obesity - Google Patents
Preparation and use of aryl alkyl acid derivatives for the treatment of obesity Download PDFInfo
- Publication number
- AU2004238258A1 AU2004238258A1 AU2004238258A AU2004238258A AU2004238258A1 AU 2004238258 A1 AU2004238258 A1 AU 2004238258A1 AU 2004238258 A AU2004238258 A AU 2004238258A AU 2004238258 A AU2004238258 A AU 2004238258A AU 2004238258 A1 AU2004238258 A1 AU 2004238258A1
- Authority
- AU
- Australia
- Prior art keywords
- biphenyl
- amino
- carboxylic acid
- carbonyl
- cyclopentane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims description 31
- 239000002253 acid Substances 0.000 title claims description 30
- 208000008589 Obesity Diseases 0.000 title claims description 29
- 235000020824 obesity Nutrition 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 215
- 150000001875 compounds Chemical class 0.000 claims description 207
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 159
- -1 1-piperidinylcarbonyl Chemical group 0.000 claims description 135
- 238000000034 method Methods 0.000 claims description 100
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 95
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 238000009472 formulation Methods 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000008177 pharmaceutical agent Substances 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- 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 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 9
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 8
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 7
- 229910005965 SO 2 Inorganic materials 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 6
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
- 102100040918 Pro-glucagon Human genes 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 208000029078 coronary artery disease Diseases 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 4
- RPGOKSGWOZBYFF-UHFFFAOYSA-N 4-[4-[4-(1,3-benzothiazol-2-ylamino)phenyl]phenyl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CC(C)(C)C(O)=O)=CC=C1C(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 RPGOKSGWOZBYFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 239000005541 ACE inhibitor Substances 0.000 claims description 4
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- 102000004877 Insulin Human genes 0.000 claims description 4
- 108090001061 Insulin Proteins 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
- 229940125396 insulin Drugs 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 3
- MOYFZIZGYGZWJT-UHFFFAOYSA-N 4-[4-[4-(1,3-benzoxazol-2-ylamino)phenyl]phenyl]-4-oxo-2-(2-phenylethyl)butanoic acid Chemical compound C=1C=C(C=2C=CC(NC=3OC4=CC=CC=C4N=3)=CC=2)C=CC=1C(=O)CC(C(=O)O)CCC1=CC=CC=C1 MOYFZIZGYGZWJT-UHFFFAOYSA-N 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
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- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 claims description 3
- 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002220 antihypertensive agent Substances 0.000 claims description 3
- 229910000085 borane Inorganic materials 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 229940125753 fibrate Drugs 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 claims description 3
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- VFKRRRPFLRUITM-WOJBJXKFSA-N (1r,2r)-2-[4-[3-fluoro-4-[(6-methoxy-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(C(=C1)F)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O VFKRRRPFLRUITM-WOJBJXKFSA-N 0.000 claims description 2
- AOHBCGJOPIUWAT-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(5-methyl-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclohexane-1-carboxylic acid Chemical compound N=1C2=CC(C)=CC=C2OC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCCC[C@H]1C(O)=O AOHBCGJOPIUWAT-DHIUTWEWSA-N 0.000 claims description 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 38
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Applications Claiming Priority (3)
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| US46961903P | 2003-05-09 | 2003-05-09 | |
| US60/469,619 | 2003-05-09 | ||
| PCT/US2004/014036 WO2004100881A2 (en) | 2003-05-09 | 2004-05-06 | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
Publications (1)
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| AU2004238258A1 true AU2004238258A1 (en) | 2004-11-25 |
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| AU2004238258A Abandoned AU2004238258A1 (en) | 2003-05-09 | 2004-05-06 | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
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| US20090048258A1 (en) * | 2005-02-01 | 2009-02-19 | Masaki Ogino | Amide Compound |
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| KR20080000652A (ko) * | 2005-04-19 | 2008-01-02 | 바이엘 파마슈티칼스 코포레이션 | 아릴 알킬산 유도체 및 그의 용도 |
| KR20080015113A (ko) * | 2005-06-11 | 2008-02-18 | 아스트라제네카 아베 | Dgat 억제제로서의 옥사디아졸 유도체 |
| JP2009505962A (ja) * | 2005-07-29 | 2009-02-12 | バイエル・ヘルスケア・エルエルシー | 肥満を治療するためのビフェニルアミノ酸誘導体の製造および使用 |
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| GB0611506D0 (en) * | 2006-06-10 | 2006-07-19 | Astrazeneca Ab | Chemical compounds |
| GB0611552D0 (en) * | 2006-06-12 | 2006-07-19 | Astrazeneca Ab | Chemical compounds |
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| NZ580662A (en) | 2007-04-30 | 2012-01-12 | Abbott Lab | Inhibitors of diacylglycerol o-acyltransferase type 1 enzyme used in manufacture of medicament for treatment of diabetes or lipid associated disorders |
| BRPI0810719A8 (pt) | 2007-04-30 | 2016-03-08 | Abbott Lab | Inibidores da enzima diacilglicerol o-acetiltansferase tipo 1 |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
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| EP2242745A1 (de) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
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| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
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| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2749700A1 (en) * | 2009-01-23 | 2010-07-29 | Msd K.K. | Benzodiazepin-2-on derivatives |
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| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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