ZA200206580B - 8,8a-dihydro-indeno[1,2-d]thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament. - Google Patents

8,8a-dihydro-indeno[1,2-d]thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament. Download PDF

Info

Publication number: ZA200206580B
Authority: ZA; South Africa
Prior art keywords: alkyl; phenyl; substituted; coo; pyridyl
Prior art date: 2000-02-26

Application number

ZA200206580A

Other languages

English (en)

Inventor

Gerhard Jaehne

Hans-Jochen Lang

Matthias Gossel

Martin Bickel

Original Assignee

Aventis Pharma Gmbh

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.)

2000-02-26

Filing date

2002-08-16

Publication date

2003-05-15

2002-08-16 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2003-05-15 Publication of ZA200206580B publication Critical patent/ZA200206580B/en

Links

-1 sulphonamido Chemical group 0.000 title claims description 43
239000003814 drug Substances 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims description 5
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 description 2
150000001875 compounds Chemical class 0.000 claims description 86
229910052731 fluorine Inorganic materials 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
229910052801 chlorine Inorganic materials 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 23
229910052794 bromium Inorganic materials 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
125000001544 thienyl group Chemical group 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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
230000001539 anorectic effect Effects 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
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 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
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000000175 2-thienyl group Chemical group S1C([*])=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
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
206010061428 decreased appetite Diseases 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
150000003556 thioamides Chemical class 0.000 claims description 5
208000008589 Obesity Diseases 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
235000020824 obesity Nutrition 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
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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
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 2
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Substances 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
125000005322 morpholin-1-yl group Chemical group 0.000 claims description 2
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 2
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 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
125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
241001465754 Metazoa Species 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
239000000460 chlorine Substances 0.000 description 11
125000000896 monocarboxylic acid group Chemical group 0.000 description 11
239000000243 solution Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
239000002253 acid Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000008194 pharmaceutical composition Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 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
238000000034 method Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000000470 constituent Substances 0.000 description 4
230000001955 cumulated effect Effects 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
238000009472 formulation Methods 0.000 description 4
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
210000004080 milk Anatomy 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
235000013336 milk Nutrition 0.000 description 3
239000008267 milk Substances 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
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238000000746 purification Methods 0.000 description 3
238000007493 shaping process Methods 0.000 description 3
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
ABKBTUSIOZWGIZ-UHFFFAOYSA-N 4-[(4-chlorophenyl)sulfonylamino]benzenecarbothioamide Chemical compound C1=CC(C(=S)N)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 ABKBTUSIOZWGIZ-UHFFFAOYSA-N 0.000 description 2
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239000005711 Benzoic acid Substances 0.000 description 2
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RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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Classifications

- 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
- 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Diabetes (AREA)
Obesity (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (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)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Child & Adolescent Psychology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Indole Compounds (AREA)

ZA200206580A 2000-02-26 2002-08-16 8,8a-dihydro-indeno[1,2-d]thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament. ZA200206580B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10009311		2000-02-26

Publications (1)

Publication Number	Publication Date
ZA200206580B true ZA200206580B (en)	2003-05-15

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ZA200206580A ZA200206580B (en)	2000-02-26	2002-08-16	8,8a-dihydro-indeno[1,2-d]thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament.

Country Status (29)

Country	Link
US (2)	US6352987B2 (sk)
EP (1)	EP1261593B1 (sk)
JP (1)	JP4950405B2 (sk)
KR (1)	KR100763214B1 (sk)
CN (1)	CN1173959C (sk)
AT (1)	ATE248155T1 (sk)
AU (2)	AU4413601A (sk)
BR (1)	BR0108631A (sk)
CA (1)	CA2400704C (sk)
CZ (1)	CZ301253B6 (sk)
DE (1)	DE50100558D1 (sk)
DK (1)	DK1261593T3 (sk)
EE (1)	EE04963B1 (sk)
ES (1)	ES2206412T3 (sk)
HK (1)	HK1052515B (sk)
HR (1)	HRP20020687B1 (sk)
HU (1)	HU229137B1 (sk)
IL (1)	IL151460A (sk)
MX (1)	MXPA02007025A (sk)
NO (1)	NO323400B1 (sk)
NZ (1)	NZ520981A (sk)
PL (1)	PL202763B1 (sk)
PT (1)	PT1261593E (sk)
RS (1)	RS49933B (sk)
RU (1)	RU2263113C2 (sk)
SI (1)	SI1261593T1 (sk)
SK (1)	SK285571B6 (sk)
WO (1)	WO2001062747A1 (sk)
ZA (1)	ZA200206580B (sk)

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US7772188B2 (en)	2003-01-28	2010-08-10	Ironwood Pharmaceuticals, Inc.	Methods and compositions for the treatment of gastrointestinal disorders
US7261482B2 (en) *	2004-01-21	2007-08-28	Silverbrook Research Pty Ltd	Photofinishing system with slitting mechanism
US20080125403A1 (en)	2004-04-02	2008-05-29	Merck & Co., Inc.	Method of Treating Men with Metabolic and Anthropometric Disorders
EP2170930B3 (en)	2007-06-04	2013-10-02	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
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
JP2011522828A (ja)	2008-06-04	2011-08-04	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	胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト
AU2009270833B2 (en)	2008-07-16	2015-02-19	Bausch Health Ireland Limited	Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
CN102264228A (zh)	2008-10-22	2011-11-30	默沙东公司	用于抗糖尿病药的新的环状苯并咪唑衍生物
AU2009309037A1 (en)	2008-10-31	2010-05-06	Merck Sharp & Dohme Corp.	Novel cyclic benzimidazole derivatives useful anti-diabetic agents
AU2011218830B2 (en)	2010-02-25	2014-07-24	Merck Sharp & Dohme Corp.	Novel cyclic benzimidazole derivatives useful anti-diabetic agents
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
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2001
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- 2001-02-13 RU RU2002125673/04A patent/RU2263113C2/ru active
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- 2001-02-13 CN CNB018055877A patent/CN1173959C/zh not_active Expired - Fee Related
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2002
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Also Published As

Publication number	Publication date
HK1052515B (zh)	2005-04-22
RU2263113C2 (ru)	2005-10-27
JP4950405B2 (ja)	2012-06-13
SI1261593T1 (en)	2004-02-29
US20010039278A1 (en)	2001-11-08
JP2003531117A (ja)	2003-10-21
US20020103231A1 (en)	2002-08-01
EE04963B1 (et)	2008-02-15
NO20023977L (no)	2002-10-18
BR0108631A (pt)	2002-12-03
YU56402A (sh)	2005-11-28
US6444669B1 (en)	2002-09-03
PT1261593E (pt)	2004-01-30
HUP0300304A3 (en)	2004-10-28
CZ20022861A3 (cs)	2002-11-13
HRP20020687B1 (en)	2011-01-31
WO2001062747A1 (de)	2001-08-30
CN1173959C (zh)	2004-11-03
EP1261593B1 (de)	2003-08-27
SK285571B6 (sk)	2007-04-05
NO20023977D0 (no)	2002-08-21
US6352987B2 (en)	2002-03-05
AU4413601A (en)	2001-09-03
EE200200467A (et)	2003-12-15
DK1261593T3 (da)	2003-12-01
EP1261593A1 (de)	2002-12-04
NO323400B1 (no)	2007-04-23
RU2002125673A (ru)	2004-01-10
NZ520981A (en)	2004-08-27
RS49933B (sr)	2008-09-29
MXPA02007025A (es)	2003-03-27
HUP0300304A2 (hu)	2003-06-28
PL202763B1 (pl)	2009-07-31
HK1052515A1 (en)	2003-09-19
CA2400704A1 (en)	2001-08-30
ES2206412T3 (es)	2004-05-16
CZ301253B6 (cs)	2009-12-23
HU229137B1 (en)	2013-08-28
ATE248155T1 (de)	2003-09-15
KR100763214B1 (ko)	2007-10-08
PL357195A1 (en)	2004-07-26
CA2400704C (en)	2008-11-04
CN1406234A (zh)	2003-03-26
DE50100558D1 (de)	2003-10-02
IL151460A (en)	2008-08-07
KR20020079897A (ko)	2002-10-19
HRP20020687A2 (en)	2004-12-31
SK12252002A3 (sk)	2003-03-04
AU2001244136B2 (en)	2005-04-14

Publication	Publication Date	Title
CA2400704C (en)	2008-11-04	8,8a-dihydro-indeno[1,2-d]thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament
AU781003B2 (en)	2005-04-28	8,8A-dihydro-indeno(1,2-D)thiazole derivatives, substituted in position 8A, a method for their production and their use as medicaments, e.g. anorectic agents
ZA200102446B (en)	2001-09-28	Indeno-, naphto- and benzocyclohepta dihydrothiazole derivatives, the production thereof and their use as anorectic medicaments.
US6387935B1 (en)	2002-05-14	Polycyclic dihydrothiazoles having substituted alkyl radicals in the two-position, process for their preparation, and their use as pharmaceuticals
US6410577B2 (en)	2002-06-25	Substituted 8,8a-dihydro-3ah-indeno[1,2-d]thiazoles, processes for their preparation and their use as medicaments
ZA200203480B (en)	2002-11-27	Indeno-, naphtho-, and benzocyclohepta-dihydrothiazole derivatives, the production thereof and their use as anorectic medicaments.