ZA200303748B - Fused heteroaromatic glucokinase activators. - Google Patents
Fused heteroaromatic glucokinase activators. Download PDFInfo
- Publication number
- ZA200303748B ZA200303748B ZA200303748A ZA200303748A ZA200303748B ZA 200303748 B ZA200303748 B ZA 200303748B ZA 200303748 A ZA200303748 A ZA 200303748A ZA 200303748 A ZA200303748 A ZA 200303748A ZA 200303748 B ZA200303748 B ZA 200303748B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclopentyl
- propionamide
- phenyl
- methanesulfonyl
- compound
- Prior art date
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- 102000030595 Glucokinase Human genes 0.000 title description 21
- 108010021582 Glucokinase Proteins 0.000 title description 21
- 239000012190 activator Substances 0.000 title description 4
- 125000001072 heteroaryl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 55
- 150000001408 amides Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- -1 alkyl sulfone Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 229940080818 propionamide Drugs 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- SOYSPEAIZRNEAT-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-quinolin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 SOYSPEAIZRNEAT-UHFFFAOYSA-N 0.000 claims description 4
- AWINNBCBCPJDHB-UHFFFAOYSA-N 2-(3-cyano-4-methylsulfonylphenyl)-3-cyclopentyl-n-quinolin-2-ylpropanamide Chemical compound C1=C(C#N)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 AWINNBCBCPJDHB-UHFFFAOYSA-N 0.000 claims description 4
- NPIXKNXGHOZWPG-UHFFFAOYSA-N 3-cyclopentyl-2-(3,4-dichlorophenyl)-n-quinolin-2-ylpropanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 NPIXKNXGHOZWPG-UHFFFAOYSA-N 0.000 claims description 4
- VDCMBEAIYGSKSX-UHFFFAOYSA-N 3-cyclopentyl-2-(4-methylsulfonyl-3-nitrophenyl)-n-quinolin-2-ylpropanamide Chemical compound C1=C([N+]([O-])=O)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 VDCMBEAIYGSKSX-UHFFFAOYSA-N 0.000 claims description 4
- RBFUJKPDVLOKBZ-UHFFFAOYSA-N 3-cyclopentyl-2-(4-methylsulfonylphenyl)-n-quinolin-2-ylpropanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 RBFUJKPDVLOKBZ-UHFFFAOYSA-N 0.000 claims description 4
- VXZQZJYMVXNSMK-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1NC2=CC=CC=C2N=1)CC1CCCC1 VXZQZJYMVXNSMK-UHFFFAOYSA-N 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- SOYSPEAIZRNEAT-LJQANCHMSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-quinolin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 SOYSPEAIZRNEAT-LJQANCHMSA-N 0.000 claims description 3
- QQZSSOYUTMZBTM-MRXNPFEDSA-N (2r)-n-(1,3-benzothiazol-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 QQZSSOYUTMZBTM-MRXNPFEDSA-N 0.000 claims description 3
- QZZFVLPXDBVTEZ-UHFFFAOYSA-N 2-(3-bromo-4-methylsulfonylphenyl)-3-cyclopentyl-n-quinolin-2-ylpropanamide Chemical compound C1=C(Br)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 QZZFVLPXDBVTEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- CBSDSSJLVTWRIQ-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-2-(3-cyano-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(C#N)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 CBSDSSJLVTWRIQ-UHFFFAOYSA-N 0.000 claims description 3
- KYRDLJWNZRNWSG-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-cyclopentyl-2-(4-methylsulfonylphenyl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 KYRDLJWNZRNWSG-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- AAQDRZIJUPVUDR-MRXNPFEDSA-N (2r)-n-(1,3-benzoxazol-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 AAQDRZIJUPVUDR-MRXNPFEDSA-N 0.000 claims description 2
- ACXDSKDJMZEDQU-OAHLLOKOSA-N (2r)-n-(1,3-benzoxazol-2-yl)-3-cyclopentyl-2-(3,4-dichlorophenyl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@H](C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 ACXDSKDJMZEDQU-OAHLLOKOSA-N 0.000 claims description 2
- CCEZAKRHOWJHQJ-UHFFFAOYSA-N 3-cyclopentyl-2-(3,4-dichlorophenyl)-n-(6-methylsulfonyl-1,3-benzothiazol-2-yl)propanamide Chemical compound S1C2=CC(S(=O)(=O)C)=CC=C2N=C1NC(=O)C(C=1C=C(Cl)C(Cl)=CC=1)CC1CCCC1 CCEZAKRHOWJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- QQZSSOYUTMZBTM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 QQZSSOYUTMZBTM-UHFFFAOYSA-N 0.000 claims description 2
- OBWANNDHEQDAJQ-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-cyclopentyl-2-(3,4-dichlorophenyl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 OBWANNDHEQDAJQ-UHFFFAOYSA-N 0.000 claims description 2
- SKOFSWUZPQBFAM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-cyclopentyl-2-(4-methylsulfonyl-3-nitrophenyl)propanamide Chemical compound C1=C([N+]([O-])=O)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 SKOFSWUZPQBFAM-UHFFFAOYSA-N 0.000 claims description 2
- RNCVQIUDLLDVEL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-cyclopentyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]propanamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC2=CC=CC=C2N=1)CC1CCCC1 RNCVQIUDLLDVEL-UHFFFAOYSA-N 0.000 claims description 2
- AAQDRZIJUPVUDR-UHFFFAOYSA-N n-(1,3-benzoxazol-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 AAQDRZIJUPVUDR-UHFFFAOYSA-N 0.000 claims description 2
- NDVQEFQAKFEDNT-UHFFFAOYSA-N n-(1,3-benzoxazol-2-yl)-3-cyclopentyl-2-(4-methylsulfonyl-3-nitrophenyl)propanamide Chemical compound C1=C([N+]([O-])=O)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 NDVQEFQAKFEDNT-UHFFFAOYSA-N 0.000 claims description 2
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- MXHYIYKLWIIIDN-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-cyano-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(C#N)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1NC2=CC=CC=C2N=1)CC1CCCC1 MXHYIYKLWIIIDN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
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- NPIXKNXGHOZWPG-GOSISDBHSA-N (2r)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-quinolin-2-ylpropanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@H](C(=O)NC=1N=C2C=CC=CC2=CC=1)CC1CCCC1 NPIXKNXGHOZWPG-GOSISDBHSA-N 0.000 claims 1
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- DAFGCELMAUAKCZ-UHFFFAOYSA-N 3-cyclopentyl-2-(3,4-dichlorophenyl)-n-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C(=O)NC=1SC=2CCCCC=2N=1)CC1CCCC1 DAFGCELMAUAKCZ-UHFFFAOYSA-N 0.000 claims 1
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- 235000012054 meals Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- XGRBXFPWATYYSK-UHFFFAOYSA-N n-(1,3-benzoxazol-2-yl)-2-(3-bromo-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Br)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 XGRBXFPWATYYSK-UHFFFAOYSA-N 0.000 description 1
- CXKICAVMPHVLQN-UHFFFAOYSA-N n-(1,3-benzoxazol-2-yl)-2-(3-cyano-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(C#N)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1OC2=CC=CC=C2N=1)CC1CCCC1 CXKICAVMPHVLQN-UHFFFAOYSA-N 0.000 description 1
- IEDAZVJYMUBPHE-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-3-cyclopentyl-2-(4-methylsulfonylphenyl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1NC2=CC=CC=C2N=1)CC1CCCC1 IEDAZVJYMUBPHE-UHFFFAOYSA-N 0.000 description 1
- 210000004738 parenchymal cell Anatomy 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 230000029964 regulation of glucose metabolic process Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
Classifications
-
- 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
- C07D215/16—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 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
- C07D215/38—Nitrogen atoms
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25163700P | 2000-12-06 | 2000-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303748B true ZA200303748B (en) | 2004-08-16 |
Family
ID=22952803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303748A ZA200303748B (en) | 2000-12-06 | 2003-05-14 | Fused heteroaromatic glucokinase activators. |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US6545155B2 (enExample) |
| EP (1) | EP1341774B1 (enExample) |
| JP (1) | JP4109111B2 (enExample) |
| KR (1) | KR100545431B1 (enExample) |
| CN (1) | CN1226294C (enExample) |
| AR (1) | AR031627A1 (enExample) |
| AT (1) | ATE316965T1 (enExample) |
| AU (2) | AU2002221902B2 (enExample) |
| BR (1) | BR0115999A (enExample) |
| CA (1) | CA2429642C (enExample) |
| DE (1) | DE60117059T2 (enExample) |
| DK (1) | DK1341774T3 (enExample) |
| ES (1) | ES2256340T3 (enExample) |
| GT (1) | GT200100243A (enExample) |
| MX (1) | MXPA03005119A (enExample) |
| PA (1) | PA8534301A1 (enExample) |
| PE (1) | PE20020753A1 (enExample) |
| PT (1) | PT1341774E (enExample) |
| UY (1) | UY27055A1 (enExample) |
| WO (1) | WO2002046173A1 (enExample) |
| ZA (1) | ZA200303748B (enExample) |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| RU2340605C2 (ru) | 2002-06-27 | 2008-12-10 | Ново Нордиск А/С | Арилкарбонильные производные в качестве терапевтических средств |
| EP1531815B1 (en) * | 2002-06-27 | 2014-09-24 | Novo Nordisk A/S | Glucokinase activators |
| US6775812B2 (en) * | 2002-07-17 | 2004-08-10 | Hewlett-Packard Development Company, L.P. | Layout design process and system for providing bypass capacitance and compliant density in an integrated circuit |
| PL375149A1 (en) | 2002-10-03 | 2005-11-28 | F.Hoffmann-La Roche Ag | Indole-3-carboxamides as glucokinase (gk) activators |
| RU2005113713A (ru) * | 2002-10-03 | 2006-01-20 | Новартис АГ (CH) | Замещенные (тиазол-2-ил)амиды или сульфонамиды в качестве активаторов глюкокиназы, которые могут применяться при лечении диабета типа 2 |
| GB0226931D0 (en) * | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| GB0226930D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| US7132425B2 (en) | 2002-12-12 | 2006-11-07 | Hoffmann-La Roche Inc. | 5-substituted-six-membered heteroaromatic glucokinase activators |
| PL378117A1 (pl) * | 2003-02-11 | 2006-03-06 | Prosidion Limited | Tricyklopodstawione związki amidowe |
| JP4621198B2 (ja) * | 2003-02-11 | 2011-01-26 | プロシディオン・リミテッド | トリ（シクロ）置換アミドグルコキナーゼ活性化化合物 |
| ATE390922T1 (de) * | 2003-06-20 | 2008-04-15 | Hoffmann La Roche | 2-aminobenzothiazole als cb1 rezeptor inverse agonisten |
| WO2005066145A1 (en) | 2004-01-06 | 2005-07-21 | Novo Nordisk A/S | Heteroaryl-ureas and their use as glucokinase activators |
| US20080312207A1 (en) * | 2004-02-18 | 2008-12-18 | Craig Johnstone | Compounds |
| ES2322709T3 (es) * | 2004-02-18 | 2009-06-25 | Astrazeneca Ab | Derivados de benzamida y su uso como agentes activadores de la glucocinasa. |
| WO2005095417A1 (en) * | 2004-04-02 | 2005-10-13 | Novartis Ag | Thiazolopyridine derivates, pharmaceutical conditions containing them and methods of treating glucokinase mediated conditions |
| ATE524479T1 (de) * | 2004-04-02 | 2011-09-15 | Novartis Ag | Sulfonamidthiazolpyridinderivate als zur behandlung von typ-2-diabetes geeignete glucokinaseaktivatoren |
| NZ550567A (en) * | 2004-04-21 | 2010-07-30 | Prosidion Ltd | Tri(cyclo) substituted amide compounds |
| TW200600086A (en) * | 2004-06-05 | 2006-01-01 | Astrazeneca Ab | Chemical compound |
| AU2005271016A1 (en) | 2004-08-12 | 2006-02-16 | Prosidion Limited | Substituted phenylacetamides and their use as glucokinase activators |
| AU2005293343B2 (en) | 2004-10-16 | 2009-03-19 | Astrazeneca Ab | Process for making phenoxy benzamide compounds |
| GB0423043D0 (en) * | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| GB0423044D0 (en) * | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| KR20070083939A (ko) * | 2004-11-02 | 2007-08-24 | 반유 세이야꾸 가부시끼가이샤 | 아릴옥시 치환된 벤즈이미다졸 유도체 |
| DE102005012872A1 (de) * | 2005-03-19 | 2006-09-28 | Sanofi-Aventis Deutschland Gmbh | Substituierte, bizyklische 8-Pyrrolidino-benzimidazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US20110059941A1 (en) * | 2005-05-24 | 2011-03-10 | Peter William Rodney Caulkett | 2-phenyl substituted imidazol [4,5b] pyridine/pyrazine and purine derivatives as glucokinase modulators |
| TW200714597A (en) * | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
| EP2027113A1 (en) * | 2005-07-09 | 2009-02-25 | AstraZeneca AB | Heteroaryl benzamide derivatives for use as glk activators in the treatment of diabetes |
| BRPI0622261A2 (pt) | 2005-07-09 | 2011-08-09 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, processo para a preparação de um composto |
| EP1910350A1 (en) * | 2005-07-09 | 2008-04-16 | AstraZeneca AB | 2 -heterocyclyloxybenzoyl amino heterocyclyl compounds as modulators of glucokinase for the treatment of type 2 diabetes |
| WO2007007910A1 (ja) * | 2005-07-13 | 2007-01-18 | Banyu Pharmaceutical Co., Ltd. | ヘテロ環置換ベンズイミダゾール誘導体 |
| US9202182B2 (en) * | 2005-08-11 | 2015-12-01 | International Business Machines Corporation | Method and system for analyzing business architecture |
| JP2007063225A (ja) | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
| RU2008112198A (ru) | 2005-09-29 | 2009-10-10 | Санофи-Авентис (Fr) | Производные фенил-1,2,4-оксадиазолона, способы их получения и их применение в качестве фармацевтических средств |
| GT200600428A (es) * | 2005-09-30 | 2007-05-21 | Compuestos organicos | |
| GT200600429A (es) * | 2005-09-30 | 2007-04-30 | Compuestos organicos | |
| US20090005391A1 (en) * | 2005-11-03 | 2009-01-01 | Matthew Colin Thor Fyfe | Tricyclo Substituted Amides |
| EP1948614A2 (en) * | 2005-11-18 | 2008-07-30 | Takeda San Diego, Inc. | Glucokinase activators |
| TW200738621A (en) * | 2005-11-28 | 2007-10-16 | Astrazeneca Ab | Chemical process |
| AT503354B1 (de) * | 2006-02-22 | 2008-07-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von 3,4-disubstituierten phenylessigsäuren, sowie neue zwischenverbindungen |
| EP2001875A2 (en) | 2006-03-08 | 2008-12-17 | Takeda San Diego, Inc. | Glucokinase activators |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| ATE522518T1 (de) | 2006-05-31 | 2011-09-15 | Takeda San Diego Inc | Indazol- und isoindolderivate als glucokinaseaktivierende stoffe |
| US7888504B2 (en) | 2006-07-06 | 2011-02-15 | Bristol-Myers Squibb Company | Glucokinase activators and methods of using same |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| BRPI0715531A2 (pt) | 2006-07-24 | 2014-06-24 | Hoffmann La Roche | Composto, composição farmacêutica, método para o tratamento de uma enfermidade e/ou distúrbio metabólico, processo para a preparação de compostos e uso do composto |
| TW200825063A (en) * | 2006-10-23 | 2008-06-16 | Astrazeneca Ab | Chemical compounds |
| CL2007003061A1 (es) * | 2006-10-26 | 2008-08-01 | Astrazeneca Ab | Compuestos derivados de 3,5-dioxi-benzamida; proceso de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar una enfermedad mediada a traves de glk, tal como la diabetes tipo 2. |
| US8163779B2 (en) | 2006-12-20 | 2012-04-24 | Takeda San Diego, Inc. | Glucokinase activators |
| RU2009121756A (ru) * | 2006-12-21 | 2011-01-27 | Астразенека Аб (Se) | Новое кристаллическое соединение, полезное в качестве активатора глюкокиназы (glk) |
| TW200831081A (en) * | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
| WO2008111473A1 (ja) * | 2007-03-07 | 2008-09-18 | Kyorin Pharmaceutical Co., Ltd. | グルコキナーゼ活性化物質 |
| WO2008116107A2 (en) | 2007-03-21 | 2008-09-25 | Takeda San Diego, Inc. | Piperazine derivatives as glucokinase activators |
| CL2009000004A1 (es) * | 2008-01-15 | 2010-02-19 | Lilly Co Eli | Forma cristalina de r-2-(4-ciclopropansulfonil-fenil)-n-pirazin-2-il-3-(tetrahidropiran-4-il)-propionamida; composicion farmaceutica que comprende a dicha forma cristalina; y uso para el tratamiento de diabetes o hiperglicemia. |
| KR20100113518A (ko) | 2008-01-18 | 2010-10-21 | 아스텔라스세이야쿠 가부시키가이샤 | 페닐아세트아미드 유도체 |
| US8258134B2 (en) | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| SI2275414T1 (sl) | 2008-04-28 | 2015-10-30 | Kyorin Pharmaceutical Co., Ltd., | Ciklopentilakrilamidni derivat |
| KR20110052676A (ko) | 2008-08-04 | 2011-05-18 | 아스트라제네카 아베 | 피라졸로[3,4]피리미딘-4-일 유도체 및 당뇨병 및 비만을 치료하기 위한 이의 용도 |
| JP5937353B2 (ja) * | 2008-08-19 | 2016-06-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | 冷感−メントール受容体拮抗剤 |
| EA201100311A1 (ru) | 2008-09-11 | 2011-10-31 | Пфайзер Инк. | Амидные производные гетероарилов и их применение в качестве активаторов глюкокиназы |
| GB0902406D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Crystalline polymorphic form |
| GB0902434D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Chemical process |
| EP2604604A1 (en) | 2009-03-11 | 2013-06-19 | Pfizer Inc | Benzofuranyl derivatives used as glucokinase inhibitors |
| AR076221A1 (es) | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | Derivado de pirazol [4,5-e] pirimidina y su uso para tratar diabetes y obesidad |
| AR076220A1 (es) | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | Derivados de pirazol [4,5 - e] pirimidina |
| US8222416B2 (en) * | 2009-12-14 | 2012-07-17 | Hoffmann-La Roche Inc. | Azaindole glucokinase activators |
| ES2893699T3 (es) | 2010-03-31 | 2022-02-09 | Scripps Research Inst | Reprogramación de células |
| US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EP3366698A1 (en) | 2011-03-01 | 2018-08-29 | Synergy Pharmaceuticals Inc. | Guanylate cyclase c agonists |
| ES2489297B1 (es) | 2013-01-22 | 2015-06-10 | Consejo Superior De Investigaciones Científicas (Csic) | Benzotiazoles sustituidos y sus aplicaciones terapeuticas para el tratamiento de enfermedades humanas |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| EP2878339A1 (en) | 2013-12-02 | 2015-06-03 | Siena Biotech S.p.A. | SIP3 antagonists |
| MX389591B (es) | 2014-08-29 | 2025-03-20 | Tes Pharma S R L | INHIBIDORES DE ACIDO A-AMINO-ß-CARBOXIMUCONICO SEMIALDEHIDO DESCARBOXILASA |
| JP6684516B2 (ja) | 2015-05-15 | 2020-04-22 | オーリジーン ディスカバリー テクノロジーズ リミテッドＡｕｒｉｇｅｎｅ Ｄｉｓｃｏｖｅｒｙ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｌｉｍｉｔｅｄ | Ｒｏｒガンマ調節物質としての置換型テトラヒドロキノリン化合物 |
| US20180134667A1 (en) | 2016-10-14 | 2018-05-17 | TES Pharma S.r.I. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
| CA3093025A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| AR117122A1 (es) | 2018-11-20 | 2021-07-14 | Tes Pharma S R L | INHIBIDORES DE LA ÁCIDO a-AMINO-b-CARBOXIMUCÓNICO SEMIALDEHÍDO DESCARBOXILASA |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| MX2022015525A (es) | 2020-06-08 | 2023-03-23 | Vtv Therapeutics Llc | Sales o co-cristales del acido {2-[3-ciclohexil-3-(trans-4-propoxi ciclohexil)ureido]tiazol-5-ilsulfanil}acetico y usos de los mismos. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3840550A (en) * | 1971-05-24 | 1974-10-08 | Ciba Geigy Corp | Certain 6-isothiocyanobenzothiazoles |
| CN1151140C (zh) * | 1999-03-29 | 2004-05-26 | 霍夫曼-拉罗奇有限公司 | 葡糖激酶活化剂 |
| US6320050B1 (en) * | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
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2001
- 2001-11-28 JP JP2002547912A patent/JP4109111B2/ja not_active Expired - Fee Related
- 2001-11-28 DK DK01999565T patent/DK1341774T3/da active
- 2001-11-28 ES ES01999565T patent/ES2256340T3/es not_active Expired - Lifetime
- 2001-11-28 KR KR1020037007517A patent/KR100545431B1/ko not_active Expired - Fee Related
- 2001-11-28 EP EP01999565A patent/EP1341774B1/en not_active Expired - Lifetime
- 2001-11-28 AU AU2002221902A patent/AU2002221902B2/en not_active Ceased
- 2001-11-28 CA CA002429642A patent/CA2429642C/en not_active Expired - Fee Related
- 2001-11-28 PT PT01999565T patent/PT1341774E/pt unknown
- 2001-11-28 WO PCT/EP2001/013870 patent/WO2002046173A1/en not_active Ceased
- 2001-11-28 DE DE60117059T patent/DE60117059T2/de not_active Expired - Lifetime
- 2001-11-28 AT AT01999565T patent/ATE316965T1/de not_active IP Right Cessation
- 2001-11-28 BR BR0115999-2A patent/BR0115999A/pt not_active IP Right Cessation
- 2001-11-28 AU AU2190202A patent/AU2190202A/xx active Pending
- 2001-11-28 CN CNB018194494A patent/CN1226294C/zh not_active Expired - Fee Related
- 2001-12-04 US US10/006,170 patent/US6545155B2/en not_active Expired - Fee Related
- 2001-12-04 PE PE2001001217A patent/PE20020753A1/es not_active Application Discontinuation
- 2001-12-04 PA PA20018534301A patent/PA8534301A1/es unknown
- 2001-12-04 AR ARP010105639A patent/AR031627A1/es unknown
- 2001-12-04 US US10/007,091 patent/US6448399B1/en not_active Expired - Fee Related
- 2001-12-04 US US10/006,168 patent/US6441184B1/en not_active Expired - Fee Related
- 2001-12-05 UY UY27055A patent/UY27055A1/es not_active Application Discontinuation
- 2001-12-05 GT GT200100243A patent/GT200100243A/es unknown
-
2003
- 2003-05-14 ZA ZA200303748A patent/ZA200303748B/en unknown
- 2003-06-06 MX MXPA03005119A patent/MXPA03005119A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| DE60117059T2 (de) | 2006-10-26 |
| CN1476438A (zh) | 2004-02-18 |
| DE60117059D1 (de) | 2006-04-13 |
| US6448399B1 (en) | 2002-09-10 |
| PE20020753A1 (es) | 2002-08-27 |
| CA2429642C (en) | 2007-11-20 |
| CA2429642A1 (en) | 2002-06-13 |
| DK1341774T3 (da) | 2006-06-12 |
| CN1226294C (zh) | 2005-11-09 |
| US20020107396A1 (en) | 2002-08-08 |
| KR20030068555A (ko) | 2003-08-21 |
| JP2004517087A (ja) | 2004-06-10 |
| AU2002221902B2 (en) | 2006-11-23 |
| PA8534301A1 (es) | 2002-08-26 |
| US20020103241A1 (en) | 2002-08-01 |
| AR031627A1 (es) | 2003-09-24 |
| EP1341774B1 (en) | 2006-02-01 |
| KR100545431B1 (ko) | 2006-01-24 |
| WO2002046173A1 (en) | 2002-06-13 |
| EP1341774A1 (en) | 2003-09-10 |
| PT1341774E (pt) | 2006-05-31 |
| AU2190202A (en) | 2002-06-18 |
| MXPA03005119A (es) | 2004-10-15 |
| ATE316965T1 (de) | 2006-02-15 |
| UY27055A1 (es) | 2002-07-31 |
| JP4109111B2 (ja) | 2008-07-02 |
| BR0115999A (pt) | 2003-09-30 |
| US20020103199A1 (en) | 2002-08-01 |
| ES2256340T3 (es) | 2006-07-16 |
| US6545155B2 (en) | 2003-04-08 |
| GT200100243A (es) | 2002-06-04 |
| US6441184B1 (en) | 2002-08-27 |
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