AU2005296958A1 - 2-amido-4-phenylthiazole derivatives, the preparation and the therapeutic use thereof - Google Patents
2-amido-4-phenylthiazole derivatives, the preparation and the therapeutic use thereof Download PDFInfo
- Publication number
- AU2005296958A1 AU2005296958A1 AU2005296958A AU2005296958A AU2005296958A1 AU 2005296958 A1 AU2005296958 A1 AU 2005296958A1 AU 2005296958 A AU2005296958 A AU 2005296958A AU 2005296958 A AU2005296958 A AU 2005296958A AU 2005296958 A1 AU2005296958 A1 AU 2005296958A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- group
- thiazol
- alkoxy
- methoxyphenyl
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims description 43
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 142
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 23
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 14
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 14
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims description 13
- 125000000815 N-oxide group Chemical group 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- HZXWLKUJDKRBQF-UHFFFAOYSA-N 4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound COC1=CC=C(C2CCCCC2)C=C1C1=CSC(N)=N1 HZXWLKUJDKRBQF-UHFFFAOYSA-N 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-UHFFFAOYSA-N 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 7
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000005336 allyloxy group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- ACNPMHHSEMHUGY-UHFFFAOYSA-N 4-(5-butyl-2-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound CCCCC1=CC=C(OC)C(C=2N=C(N)SC=2)=C1 ACNPMHHSEMHUGY-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- LKIZXBUWQPNTQF-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-4-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(CC1)CCN1C(=O)C1=CN=CC=N1 LKIZXBUWQPNTQF-UHFFFAOYSA-N 0.000 claims description 3
- LNXRZYHWTAUMHY-MRVPVSSYSA-N (3r)-1-(pyrazine-2-carbonyl)piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1C(=O)C1=CN=CC=N1 LNXRZYHWTAUMHY-MRVPVSSYSA-N 0.000 claims description 2
- LNXRZYHWTAUMHY-QMMMGPOBSA-N (3s)-1-(pyrazine-2-carbonyl)piperidine-3-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCCN1C(=O)C1=CN=CC=N1 LNXRZYHWTAUMHY-QMMMGPOBSA-N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
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- 230000001154 acute effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 230000002491 angiogenic effect Effects 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- POAIOYTYGFGBOY-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-ethoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound CCOC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 POAIOYTYGFGBOY-UHFFFAOYSA-N 0.000 claims description 2
- UGAMCDRWOXXFRA-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(1-methylimidazole-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=NC=CN1C UGAMCDRWOXXFRA-UHFFFAOYSA-N 0.000 claims description 2
- KEFVPSJTLZONNL-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(furan-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=CO1 KEFVPSJTLZONNL-UHFFFAOYSA-N 0.000 claims description 2
- AEEPZDSCOILTDI-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-2-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C1CCCCN1C(=O)C1=CN=CC=N1 AEEPZDSCOILTDI-UHFFFAOYSA-N 0.000 claims description 2
- UZGCRIGUQOVVFR-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 UZGCRIGUQOVVFR-UHFFFAOYSA-N 0.000 claims description 2
- GCNRKXBJZHYOQD-UHFFFAOYSA-N n-[4-(5-cyclopentyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 GCNRKXBJZHYOQD-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GJYGAFGYZQSTMH-UHFFFAOYSA-N 1-(5-chloro-1-methylpyrazole-4-carbonyl)-n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C=1C=NN(C)C=1Cl GJYGAFGYZQSTMH-UHFFFAOYSA-N 0.000 claims 1
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- KZJNCUDYCCMESU-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(1,5-dimethylpyrazole-3-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C=1C=C(C)N(C)N=1 KZJNCUDYCCMESU-UHFFFAOYSA-N 0.000 claims 1
- AEXQESOTSPPIIR-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(2-oxo-1h-pyridine-3-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=CN=C1O AEXQESOTSPPIIR-UHFFFAOYSA-N 0.000 claims 1
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- DEEOSPIQFYSNIA-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrimidine-4-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=NC=N1 DEEOSPIQFYSNIA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0411083 | 2004-10-19 | ||
| FR0411083A FR2876692B1 (fr) | 2004-10-19 | 2004-10-19 | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| PCT/FR2005/002565 WO2006042954A1 (fr) | 2004-10-19 | 2005-10-17 | Dérivés de 2-amido-4-phenylthiazole, leur préparation et leur application en thérapeutique |
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| AU2005296958A1 true AU2005296958A1 (en) | 2006-04-27 |
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| EP (1) | EP1807421B1 (OSRAM) |
| JP (1) | JP2008517042A (OSRAM) |
| KR (1) | KR20070085395A (OSRAM) |
| CN (1) | CN101065376A (OSRAM) |
| AR (1) | AR051334A1 (OSRAM) |
| AT (1) | ATE502035T1 (OSRAM) |
| AU (1) | AU2005296958A1 (OSRAM) |
| BR (1) | BRPI0518231A2 (OSRAM) |
| CA (1) | CA2584774A1 (OSRAM) |
| DE (1) | DE602005026964D1 (OSRAM) |
| EA (1) | EA200700901A1 (OSRAM) |
| EC (1) | ECSP077402A (OSRAM) |
| FR (1) | FR2876692B1 (OSRAM) |
| GT (1) | GT200500292A (OSRAM) |
| IL (1) | IL182624A0 (OSRAM) |
| MA (1) | MA29017B1 (OSRAM) |
| MX (1) | MX2007004740A (OSRAM) |
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| PA (1) | PA8649901A1 (OSRAM) |
| PE (1) | PE20060585A1 (OSRAM) |
| SV (1) | SV2006002274A (OSRAM) |
| TN (1) | TNSN07145A1 (OSRAM) |
| TW (1) | TW200630364A (OSRAM) |
| UY (1) | UY29169A1 (OSRAM) |
| WO (1) | WO2006042954A1 (OSRAM) |
| ZA (1) | ZA200703876B (OSRAM) |
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| FR2854158B1 (fr) | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| FR2872813B1 (fr) | 2004-07-09 | 2007-01-19 | Sanofi Synthelabo | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| JP2009519346A (ja) * | 2005-12-12 | 2009-05-14 | ジェネラブズ テクノロジーズ インコーポレーティッド | Ｎ−（５員芳香族環）−アミド抗ウイルス化合物 |
| FR2895989B1 (fr) | 2006-01-06 | 2010-04-30 | Sanofi Aventis | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| WO2009076404A1 (en) * | 2007-12-10 | 2009-06-18 | Epix Delaware, Inc. | Carboxamide compounds and their use as antagonists of the chemokine ccr2 receptor |
| AU2008335135A1 (en) | 2007-12-11 | 2009-06-18 | Cytopathfinder, Inc. | Carboxamide compounds and their use as chemokine receptor agonists |
| JP5401544B2 (ja) | 2008-07-15 | 2014-01-29 | ノバルティス アーゲー | Ｄｇａｔ１阻害剤としてのヘテロアリール誘導体 |
| MA32975B1 (fr) * | 2008-12-22 | 2012-01-02 | Chemocentryx Inc | Antagonistes de c5ar |
| WO2012093101A1 (en) | 2011-01-04 | 2012-07-12 | Novartis Ag | Indole compounds or analogues thereof useful for the treatment of age-related macular degeneration (amd) |
| CN104379579B (zh) | 2012-06-28 | 2017-03-08 | 诺华股份有限公司 | 吡咯烷衍生物及其作为补体途径调节剂的用途 |
| CN104603126B (zh) | 2012-06-28 | 2017-05-31 | 诺华股份有限公司 | 吡咯烷衍生物及其作为补体途径调节剂的用途 |
| WO2014002054A1 (en) | 2012-06-28 | 2014-01-03 | Novartis Ag | Pyrrolidine derivatives and their use as complement pathway modulators |
| WO2014002058A2 (en) | 2012-06-28 | 2014-01-03 | Novartis Ag | Complement pathway modulators and uses thereof |
| WO2014002051A2 (en) | 2012-06-28 | 2014-01-03 | Novartis Ag | Complement pathway modulators and uses thereof |
| KR20150036481A (ko) | 2012-07-12 | 2015-04-07 | 노파르티스 아게 | 보체 경로 조절제 및 그의 용도 |
| IL296139A (en) | 2020-03-03 | 2022-11-01 | Pic Therapeutics Inc | Eif4e inhibitors and uses thereof |
| AU2022334296A1 (en) | 2021-08-25 | 2024-03-07 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| WO2023028238A1 (en) | 2021-08-25 | 2023-03-02 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| WO2024191268A1 (ko) * | 2023-03-15 | 2024-09-19 | 현대약품 주식회사 | 신규한 화합물, 및 이를 포함하는 약학적 조성물 |
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| US2146898A (en) * | 1937-12-06 | 1939-02-14 | Int Harvester Co | Potato digger |
| FR2406634A1 (fr) * | 1977-10-19 | 1979-05-18 | Fabre Sa Pierre | Immunostimulants derives d'amino thiazoles |
| FR2677356B1 (fr) | 1991-06-05 | 1995-03-17 | Sanofi Sa | Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant. |
| EP0519449A1 (en) | 1991-06-21 | 1992-12-23 | Boehringer Mannheim Italia S.P.A. | 2-Amino-4-aryl thiazoles with antiasthmatic and antiinflammatory activities on the respiratory tract |
| US6506751B1 (en) * | 1999-11-12 | 2003-01-14 | Millennium Pharmaceuticals, Inc. | Thiazolidinone compounds useful as chemokine inhibitors |
| US6852752B2 (en) * | 1999-12-17 | 2005-02-08 | Vicuron Pharmaceuticals Inc. | Urea compounds, compositions and methods of use and preparation |
| US6797820B2 (en) * | 1999-12-17 | 2004-09-28 | Vicuron Pharmaceuticals Inc. | Succinate compounds, compositions and methods of use and preparation |
| EP1344525A4 (en) * | 2000-12-22 | 2005-05-25 | Ishihara Sangyo Kaisha | ANILINE DERIVATIVES OR ITS SALTS AND CYTOKINE PRODUCTION INHIBITORS CONTAINING THEM |
| WO2003015778A1 (en) | 2001-08-17 | 2003-02-27 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| FR2854158B1 (fr) * | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| TW200423931A (en) | 2003-04-30 | 2004-11-16 | Hoffmann La Roche | Novel aniline derivatives, their manufacture and use as pharmaceutical agents |
| FR2872813B1 (fr) * | 2004-07-09 | 2007-01-19 | Sanofi Synthelabo | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| JP5118975B2 (ja) | 2004-12-24 | 2013-01-16 | アストラゼネカ・アクチエボラーグ | Ｃｃｒ２ｂアンタゴニストとしてのヘテロ環式化合物 |
| FR2895989B1 (fr) | 2006-01-06 | 2010-04-30 | Sanofi Aventis | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
-
2004
- 2004-10-19 FR FR0411083A patent/FR2876692B1/fr not_active Expired - Fee Related
-
2005
- 2005-10-17 AU AU2005296958A patent/AU2005296958A1/en not_active Withdrawn
- 2005-10-17 BR BRPI0518231-0A patent/BRPI0518231A2/pt not_active IP Right Cessation
- 2005-10-17 WO PCT/FR2005/002565 patent/WO2006042954A1/fr not_active Ceased
- 2005-10-17 KR KR1020077011308A patent/KR20070085395A/ko not_active Withdrawn
- 2005-10-17 AT AT05809089T patent/ATE502035T1/de not_active IP Right Cessation
- 2005-10-17 CN CNA2005800396968A patent/CN101065376A/zh active Pending
- 2005-10-17 UY UY29169A patent/UY29169A1/es not_active Application Discontinuation
- 2005-10-17 GT GT200500292A patent/GT200500292A/es unknown
- 2005-10-17 DE DE602005026964T patent/DE602005026964D1/de not_active Expired - Lifetime
- 2005-10-17 JP JP2007537324A patent/JP2008517042A/ja active Pending
- 2005-10-17 CA CA002584774A patent/CA2584774A1/fr not_active Abandoned
- 2005-10-17 ZA ZA200703876A patent/ZA200703876B/xx unknown
- 2005-10-17 MX MX2007004740A patent/MX2007004740A/es not_active Application Discontinuation
- 2005-10-17 EA EA200700901A patent/EA200700901A1/ru unknown
- 2005-10-17 EP EP05809089A patent/EP1807421B1/fr not_active Expired - Lifetime
- 2005-10-18 AR ARP050104349A patent/AR051334A1/es unknown
- 2005-10-18 PA PA20058649901A patent/PA8649901A1/es unknown
- 2005-10-18 TW TW094136365A patent/TW200630364A/zh unknown
- 2005-10-19 PE PE2005001227A patent/PE20060585A1/es not_active Application Discontinuation
- 2005-10-19 SV SV2005002274A patent/SV2006002274A/es unknown
-
2007
- 2007-04-17 IL IL182624A patent/IL182624A0/en unknown
- 2007-04-18 EC EC2007007402A patent/ECSP077402A/es unknown
- 2007-04-18 US US11/736,770 patent/US7598392B2/en not_active Expired - Fee Related
- 2007-04-19 TN TNP2007000145A patent/TNSN07145A1/fr unknown
- 2007-05-11 MA MA29894A patent/MA29017B1/fr unknown
- 2007-05-16 NO NO20072515A patent/NO20072515L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP077402A (es) | 2007-05-30 |
| US7598392B2 (en) | 2009-10-06 |
| EP1807421A1 (fr) | 2007-07-18 |
| PE20060585A1 (es) | 2006-08-18 |
| TNSN07145A1 (fr) | 2008-11-21 |
| JP2008517042A (ja) | 2008-05-22 |
| FR2876692A1 (fr) | 2006-04-21 |
| UY29169A1 (es) | 2006-05-31 |
| PA8649901A1 (es) | 2006-06-02 |
| CN101065376A (zh) | 2007-10-31 |
| IL182624A0 (en) | 2007-07-24 |
| US20070259847A1 (en) | 2007-11-08 |
| AR051334A1 (es) | 2007-01-03 |
| ZA200703876B (en) | 2008-12-31 |
| WO2006042954A8 (fr) | 2008-03-13 |
| KR20070085395A (ko) | 2007-08-27 |
| NO20072515L (no) | 2007-06-28 |
| MX2007004740A (es) | 2007-06-18 |
| CA2584774A1 (fr) | 2006-04-27 |
| BRPI0518231A2 (pt) | 2008-11-11 |
| EP1807421B1 (fr) | 2011-03-16 |
| EA200700901A1 (ru) | 2007-10-26 |
| GT200500292A (es) | 2006-05-11 |
| SV2006002274A (es) | 2006-06-28 |
| FR2876692B1 (fr) | 2007-02-23 |
| WO2006042954A1 (fr) | 2006-04-27 |
| MA29017B1 (fr) | 2007-11-01 |
| ATE502035T1 (de) | 2011-04-15 |
| TW200630364A (en) | 2006-09-01 |
| DE602005026964D1 (de) | 2011-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: SANOFI-AVENTIS Free format text: FORMER NAME: SANOFIS-AVENTIS |
|
| MK12 | Application lapsed section 141(1)/reg 8.3(2) - applicant filed a written notice of withdrawal |