SK12162002A3 - 8,8a-Dihydroindeno [1,2-d]tiazolové driváty substituované v polohe 8a, spôsob ich prípravy a ich použitie ako liečiv - Google Patents
8,8a-Dihydroindeno [1,2-d]tiazolové driváty substituované v polohe 8a, spôsob ich prípravy a ich použitie ako liečiv Download PDFInfo
- Publication number
- SK12162002A3 SK12162002A3 SK1216-2002A SK12162002A SK12162002A3 SK 12162002 A3 SK12162002 A3 SK 12162002A3 SK 12162002 A SK12162002 A SK 12162002A SK 12162002 A3 SK12162002 A3 SK 12162002A3
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- Slovakia
- Prior art keywords
- alkyl
- group
- phenyl
- atom
- conh
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title claims 10
- 239000002830 appetite depressant Substances 0.000 title abstract description 3
- 229940125709 anorectic agent Drugs 0.000 title abstract 2
- DZMMSRPZFITCLI-UHFFFAOYSA-N 3a,4-dihydro-2h-indeno[1,2-d][1,3]thiazole Chemical class C1=CC=C2C3=NCSC3CC2=C1 DZMMSRPZFITCLI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000001153 fluoro group Chemical group F* 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- -1 C0NH 2 group Chemical group 0.000 claims description 32
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 31
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 10
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- ROMNEYAQUBNRLR-UHFFFAOYSA-N 2-(4-hydroxybiphenyl-3-yl)-4-methyl-1h-isoindole-1,3(2h)-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1C(C(=CC=1)O)=CC=1C1=CC=CC=C1 ROMNEYAQUBNRLR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 230000001539 anorectic effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fuses (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10008275 | 2000-02-23 | ||
| PCT/EP2001/001499 WO2001062746A1 (de) | 2000-02-23 | 2001-02-12 | 8,8a-DIHYDRO-INDENO[1,2-d]THIAZOL-DERIVATE, DIE IN 8a-STELLUNG SUBSTITUIERT SIND; VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL Z.B. ALS ANOREKTIKA |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK12162002A3 true SK12162002A3 (sk) | 2003-02-04 |
Family
ID=7631989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1216-2002A SK12162002A3 (sk) | 2000-02-23 | 2001-02-12 | 8,8a-Dihydroindeno [1,2-d]tiazolové driváty substituované v polohe 8a, spôsob ich prípravy a ich použitie ako liečiv |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6403624B1 (ru) |
| EP (1) | EP1259498B1 (ru) |
| JP (1) | JP4898052B2 (ru) |
| KR (1) | KR20020079891A (ru) |
| CN (1) | CN1195747C (ru) |
| AT (1) | ATE283265T1 (ru) |
| AU (1) | AU781003B2 (ru) |
| BR (1) | BR0108605A (ru) |
| CA (1) | CA2400698A1 (ru) |
| CZ (1) | CZ20022838A3 (ru) |
| DE (1) | DE50104600D1 (ru) |
| EE (1) | EE200200466A (ru) |
| ES (1) | ES2231482T3 (ru) |
| HK (1) | HK1055117A1 (ru) |
| HR (1) | HRP20020688A2 (ru) |
| HU (1) | HUP0300140A3 (ru) |
| IL (1) | IL151327A0 (ru) |
| MX (1) | MXPA02007021A (ru) |
| NO (1) | NO20023978L (ru) |
| NZ (1) | NZ520926A (ru) |
| PL (1) | PL357547A1 (ru) |
| PT (1) | PT1259498E (ru) |
| RU (1) | RU2261860C2 (ru) |
| SK (1) | SK12162002A3 (ru) |
| WO (1) | WO2001062746A1 (ru) |
| YU (1) | YU56302A (ru) |
| ZA (1) | ZA200206487B (ru) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10142660A1 (de) | 2001-08-31 | 2003-03-20 | Aventis Pharma Gmbh | Verwendung von Derivaten von C2-substituierten Indan-1-ol-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| DE10142659A1 (de) | 2001-08-31 | 2003-03-20 | Aventis Pharma Gmbh | Verwendung von mehrfach substituierten Indan-1-ol. Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010009319A2 (en) | 2008-07-16 | 2010-01-21 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CN102271509A (zh) | 2008-10-31 | 2011-12-07 | 默沙东公司 | 用于抗糖尿病药的新型环苯并咪唑衍生物 |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EP2677869B1 (en) | 2011-02-25 | 2017-11-08 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| US9580471B2 (en) | 2011-03-01 | 2017-02-28 | Synergy Pharmaceuticals, Inc. | Process of preparing guanylate cyclase C agonists |
| CA2880901A1 (en) | 2012-08-02 | 2014-02-06 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2014130608A1 (en) | 2013-02-22 | 2014-08-28 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| EP2970119B1 (en) | 2013-03-14 | 2021-11-03 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP3551176A4 (en) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | ANTIDIABETIC HETEROCYCLIC COMPOUNDS |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640358A1 (de) | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| GB9517381D0 (en) * | 1995-08-24 | 1995-10-25 | Pharmacia Spa | Aryl and heteroaryl piperazine derivatives |
| DE19844547C2 (de) * | 1998-09-29 | 2002-11-07 | Aventis Pharma Gmbh | Polycyclische Dihydrothiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE19908539A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Polycyclische 2-Amino-Dihydrothiazolsysteme, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
-
2001
- 2001-02-12 PL PL01357547A patent/PL357547A1/xx not_active Application Discontinuation
- 2001-02-12 JP JP2001562528A patent/JP4898052B2/ja not_active Expired - Fee Related
- 2001-02-12 KR KR1020027011001A patent/KR20020079891A/ko not_active Application Discontinuation
- 2001-02-12 MX MXPA02007021A patent/MXPA02007021A/es active IP Right Grant
- 2001-02-12 BR BR0108605-7A patent/BR0108605A/pt not_active IP Right Cessation
- 2001-02-12 NZ NZ520926A patent/NZ520926A/en unknown
- 2001-02-12 IL IL15132701A patent/IL151327A0/xx unknown
- 2001-02-12 RU RU2002125460/04A patent/RU2261860C2/ru not_active IP Right Cessation
- 2001-02-12 SK SK1216-2002A patent/SK12162002A3/sk unknown
- 2001-02-12 CA CA002400698A patent/CA2400698A1/en not_active Abandoned
- 2001-02-12 CZ CZ20022838A patent/CZ20022838A3/cs unknown
- 2001-02-12 AU AU56153/01A patent/AU781003B2/en not_active Ceased
- 2001-02-12 PT PT01929342T patent/PT1259498E/pt unknown
- 2001-02-12 CN CNB018054919A patent/CN1195747C/zh not_active Expired - Fee Related
- 2001-02-12 AT AT01929342T patent/ATE283265T1/de not_active IP Right Cessation
- 2001-02-12 EE EEP200200466A patent/EE200200466A/xx unknown
- 2001-02-12 EP EP01929342A patent/EP1259498B1/de not_active Expired - Lifetime
- 2001-02-12 HU HU0300140A patent/HUP0300140A3/hu unknown
- 2001-02-12 YU YU56302A patent/YU56302A/sh unknown
- 2001-02-12 DE DE50104600T patent/DE50104600D1/de not_active Expired - Lifetime
- 2001-02-12 ES ES01929342T patent/ES2231482T3/es not_active Expired - Lifetime
- 2001-02-12 WO PCT/EP2001/001499 patent/WO2001062746A1/de not_active Application Discontinuation
- 2001-02-23 US US09/790,911 patent/US6403624B1/en not_active Expired - Lifetime
-
2002
- 2002-08-14 ZA ZA200206487A patent/ZA200206487B/en unknown
- 2002-08-21 NO NO20023978A patent/NO20023978L/no not_active Application Discontinuation
- 2002-08-22 HR HRP20020688 patent/HRP20020688A2/hr not_active Application Discontinuation
-
2003
- 2003-10-15 HK HK03107412A patent/HK1055117A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1259498A1 (de) | 2002-11-27 |
| NZ520926A (en) | 2004-08-27 |
| IL151327A0 (en) | 2003-04-10 |
| HUP0300140A3 (en) | 2004-10-28 |
| EP1259498B1 (de) | 2004-11-24 |
| ES2231482T3 (es) | 2005-05-16 |
| ZA200206487B (en) | 2003-10-16 |
| CN1195747C (zh) | 2005-04-06 |
| CN1423640A (zh) | 2003-06-11 |
| MXPA02007021A (es) | 2003-03-27 |
| US20020058658A1 (en) | 2002-05-16 |
| JP4898052B2 (ja) | 2012-03-14 |
| AU5615301A (en) | 2001-09-03 |
| PT1259498E (pt) | 2005-02-28 |
| US6403624B1 (en) | 2002-06-11 |
| YU56302A (sh) | 2005-11-28 |
| JP2003528825A (ja) | 2003-09-30 |
| AU781003B2 (en) | 2005-04-28 |
| HRP20020688A2 (en) | 2004-12-31 |
| NO20023978D0 (no) | 2002-08-21 |
| CZ20022838A3 (cs) | 2002-11-13 |
| KR20020079891A (ko) | 2002-10-19 |
| BR0108605A (pt) | 2002-11-19 |
| HK1055117A1 (en) | 2003-12-24 |
| HUP0300140A2 (en) | 2003-05-28 |
| RU2002125460A (ru) | 2004-01-10 |
| PL357547A1 (en) | 2004-07-26 |
| DE50104600D1 (de) | 2004-12-30 |
| ATE283265T1 (de) | 2004-12-15 |
| EE200200466A (et) | 2003-12-15 |
| NO20023978L (no) | 2002-10-18 |
| WO2001062746A1 (de) | 2001-08-30 |
| RU2261860C2 (ru) | 2005-10-10 |
| CA2400698A1 (en) | 2001-08-30 |
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