NO323246B1 - 4-pyridyl- og 2,4-pyrimidylsubstituerte pyrrolderivater, farmasoytisk middel omfattende disse, og anvendelse av disse til fremstilling av et farmasoytisk middel. - Google Patents

4-pyridyl- og 2,4-pyrimidylsubstituerte pyrrolderivater, farmasoytisk middel omfattende disse, og anvendelse av disse til fremstilling av et farmasoytisk middel. Download PDF

Info

Publication number: NO323246B1
Authority: NO; Norway
Prior art keywords: pyridyl; pyrimidyl; mmol; ppm; ether
Prior art date: 2000-02-01

Application number

NO20023634A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023634D0 (no

NO20023634L (no

Inventor

Stefan Laufer

Hans-Guenter Striegel

Karola Tollmann

Susanne Tries

Original Assignee

Merckle 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.)

2000-02-01

Filing date

2002-07-31

Publication date

2007-02-12

2002-07-31 Application filed by Merckle Gmbh filed Critical Merckle Gmbh

2002-07-31 Publication of NO20023634D0 publication Critical patent/NO20023634D0/no

2002-09-25 Publication of NO20023634L publication Critical patent/NO20023634L/no

2007-02-12 Publication of NO323246B1 publication Critical patent/NO323246B1/no

Links

150000003233 pyrroles Chemical class 0.000 title claims abstract description 10
239000008177 pharmaceutical agent Chemical class 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 5
-1 bicyclic pyrrole derivatives Chemical class 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000001544 thienyl group Chemical group 0.000 claims abstract description 5
230000003287 optical effect Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 45
150000003254 radicals Chemical class 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
210000000987 immune system Anatomy 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
102000004127 Cytokines Human genes 0.000 abstract description 5
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210000003819 peripheral blood mononuclear cell Anatomy 0.000 abstract description 4
PHITVVVKDMNEST-UHFFFAOYSA-N [3-(4-fluorophenyl)-2-pyridin-4-yl-6,7-dihydro-5h-pyrrolizin-1-yl]methanol Chemical compound OCC1=C2CCCN2C(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 PHITVVVKDMNEST-UHFFFAOYSA-N 0.000 abstract description 3
230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 abstract description 3
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 abstract description 3
241000588724 Escherichia coli Species 0.000 abstract description 2
230000005764 inhibitory process Effects 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 abstract 1
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229940086562 Cyclooxygenase 1 inhibitor Drugs 0.000 abstract 1
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125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
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239000003255 cyclooxygenase 2 inhibitor Substances 0.000 abstract 1
239000000824 cytostatic agent Substances 0.000 abstract 1
230000001085 cytostatic effect Effects 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
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230000010534 mechanism of action Effects 0.000 abstract 1
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239000000243 solution Substances 0.000 description 61
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238000005160 1H NMR spectroscopy Methods 0.000 description 48
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239000000126 substance Substances 0.000 description 19
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238000006243 chemical reaction Methods 0.000 description 18
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238000004440 column chromatography Methods 0.000 description 17
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
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239000002244 precipitate Substances 0.000 description 10
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229910018072 Al 2 O 3 Inorganic materials 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
229910052593 corundum Inorganic materials 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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239000002253 acid Substances 0.000 description 6
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238000000338 in vitro Methods 0.000 description 6
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235000011852 gelatine desserts Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
HAJKHJOABGFIGP-UHFFFAOYSA-N indolizidine Chemical compound C1CCCN2CCCC21 HAJKHJOABGFIGP-UHFFFAOYSA-N 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
SZWLZSXCHWTRCF-UHFFFAOYSA-N n-[5-[(4-fluorophenyl)methyl]-1,3-thiazol-2-yl]-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC(S1)=CN=C1NC(=O)C1CC2=CC=CC=C2OC1 SZWLZSXCHWTRCF-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
239000003768 thromboxane synthase inhibitor Substances 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Rheumatology (AREA)
Neurology (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Oncology (AREA)
Biomedical Technology (AREA)
Communicable Diseases (AREA)
Neurosurgery (AREA)
Transplantation (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO20023634A 2000-02-01 2002-07-31 4-pyridyl- og 2,4-pyrimidylsubstituerte pyrrolderivater, farmasoytisk middel omfattende disse, og anvendelse av disse til fremstilling av et farmasoytisk middel. NO323246B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10004157A DE10004157A1 (de)	2000-02-01	2000-02-01	4-Pyridyl-und 2,4-Pyrimidinyl-substituierte Pyrrolderivate und ihre Anwendung in der Pharmazie
PCT/EP2001/001011 WO2001057042A2 (de)	2000-02-01	2001-01-31	4-pyridyl- und 2,4-pyrimidinyl-substituierte pyrrolderivate und ihre anwendung in der pharmazie

Publications (3)

Publication Number	Publication Date
NO20023634D0 NO20023634D0 (no)	2002-07-31
NO20023634L NO20023634L (no)	2002-09-25
NO323246B1 true NO323246B1 (no)	2007-02-12

Family

ID=7629335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20023634A NO323246B1 (no)	2000-02-01	2002-07-31	4-pyridyl- og 2,4-pyrimidylsubstituerte pyrrolderivater, farmasoytisk middel omfattende disse, og anvendelse av disse til fremstilling av et farmasoytisk middel.

Country Status (16)

Country	Link
US (1)	US6867211B2 (es)
EP (1)	EP1252163B1 (es)
JP (1)	JP2003525227A (es)
KR (1)	KR20030005176A (es)
CN (1)	CN1206230C (es)
AT (1)	ATE250608T1 (es)
AU (1)	AU2001230219A1 (es)
CA (1)	CA2398111C (es)
DE (2)	DE10004157A1 (es)
DK (1)	DK1252163T3 (es)
ES (1)	ES2208548T3 (es)
MX (1)	MXPA02007403A (es)
NO (1)	NO323246B1 (es)
PT (1)	PT1252163E (es)
TR (1)	TR200301898T4 (es)
WO (1)	WO2001057042A2 (es)

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DE10001166A1 (de)	2000-01-13	2001-07-19	Merckle Gmbh	Anellierte Pyrrolverbindungen, diese enthaltende pharmazeutische Mittel und deren Verwendung
EP1427410A1 (en) *	2001-08-30	2004-06-16	Merckle Gmbh	Use of annellated pyrrole compounds in the treatment of articular cartilage or subchondral bone degeneration
US6849627B2 (en)	2001-09-20	2005-02-01	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US7087615B2 (en)	2001-09-20	2006-08-08	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which provide analgesia
US6730668B2 (en) *	2001-09-20	2004-05-04	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
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EP1884239A1 (en) *	2006-07-28	2008-02-06	Merckle Gmbh	Annellated pyrrole compounds for cancer management
GB0816759D0 (en) *	2008-09-12	2008-10-22	Selcia Ltd	Compounds
US20190060286A1 (en)	2016-02-29	2019-02-28	University Of Florida Research Foundation, Incorpo	Chemotherapeutic Methods

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2000
- 2000-02-01 DE DE10004157A patent/DE10004157A1/de not_active Withdrawn
2001
- 2001-01-31 DK DK01902370T patent/DK1252163T3/da active
- 2001-01-31 US US10/182,579 patent/US6867211B2/en not_active Expired - Fee Related
- 2001-01-31 WO PCT/EP2001/001011 patent/WO2001057042A2/de not_active Ceased
- 2001-01-31 AU AU2001230219A patent/AU2001230219A1/en not_active Abandoned
- 2001-01-31 DE DE50100678T patent/DE50100678D1/de not_active Expired - Fee Related
- 2001-01-31 TR TR2003/01898T patent/TR200301898T4/xx unknown
- 2001-01-31 CA CA002398111A patent/CA2398111C/en not_active Expired - Fee Related
- 2001-01-31 CN CNB018044298A patent/CN1206230C/zh not_active Expired - Fee Related
- 2001-01-31 EP EP01902370A patent/EP1252163B1/de not_active Expired - Lifetime
- 2001-01-31 PT PT01902370T patent/PT1252163E/pt unknown
- 2001-01-31 MX MXPA02007403A patent/MXPA02007403A/es active IP Right Grant
- 2001-01-31 JP JP2001557873A patent/JP2003525227A/ja active Pending
- 2001-01-31 AT AT01902370T patent/ATE250608T1/de not_active IP Right Cessation
- 2001-01-31 ES ES01902370T patent/ES2208548T3/es not_active Expired - Lifetime
- 2001-01-31 KR KR1020027009854A patent/KR20030005176A/ko not_active Withdrawn
2002
- 2002-07-31 NO NO20023634A patent/NO323246B1/no unknown

Also Published As

Publication number	Publication date
EP1252163A2 (de)	2002-10-30
ATE250608T1 (de)	2003-10-15
EP1252163B1 (de)	2003-09-24
MXPA02007403A (es)	2004-04-05
PT1252163E (pt)	2004-02-27
DK1252163T3 (da)	2004-01-19
KR20030005176A (ko)	2003-01-17
TR200301898T4 (tr)	2004-01-21
CN1396923A (zh)	2003-02-12
AU2001230219A1 (en)	2001-08-14
DE50100678D1 (de)	2003-10-30
WO2001057042A2 (de)	2001-08-09
US6867211B2 (en)	2005-03-15
US20030153558A1 (en)	2003-08-14
JP2003525227A (ja)	2003-08-26
CN1206230C (zh)	2005-06-15
NO20023634D0 (no)	2002-07-31
WO2001057042A3 (de)	2001-12-27
CA2398111A1 (en)	2001-08-09
ES2208548T3 (es)	2004-06-16
DE10004157A1 (de)	2001-08-02
CA2398111C (en)	2008-08-12
NO20023634L (no)	2002-09-25

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