NO315648B1 - Nye metalloproteaseinhiberende laktamer, farmasöytisk preparat omfattende disse samt deres anvendelse for fremstilling av farmasöytiskepreparater - Google Patents
Nye metalloproteaseinhiberende laktamer, farmasöytisk preparat omfattende disse samt deres anvendelse for fremstilling av farmasöytiskepreparater Download PDFInfo
- Publication number
- NO315648B1 NO315648B1 NO20000783A NO20000783A NO315648B1 NO 315648 B1 NO315648 B1 NO 315648B1 NO 20000783 A NO20000783 A NO 20000783A NO 20000783 A NO20000783 A NO 20000783A NO 315648 B1 NO315648 B1 NO 315648B1
- Authority
- NO
- Norway
- Prior art keywords
- oxo
- phenyl
- hydroxy
- pyrrolidineacetamide
- methoxy
- Prior art date
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 150000003951 lactams Chemical class 0.000 title description 74
- 102000005741 Metalloproteases Human genes 0.000 title description 13
- 108010006035 Metalloproteases Proteins 0.000 title description 13
- 230000002401 inhibitory effect Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
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- -1 phenyl pyridyl Chemical group 0.000 claims description 493
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 365
- 238000006243 chemical reaction Methods 0.000 claims description 169
- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 117
- 238000002360 preparation method Methods 0.000 claims description 97
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 74
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 33
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical group 0.000 claims description 25
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
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- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 9
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
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- FUNGFFXWPXLCAC-UHFFFAOYSA-N n-hydroxy-2-(3-methyl-2-oxo-3-phenylpyrrolidin-1-yl)acetamide Chemical compound C=1C=CC=CC=1C1(C)CCN(CC(=O)NO)C1=O FUNGFFXWPXLCAC-UHFFFAOYSA-N 0.000 claims description 4
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- XIAUEHKDRHFIFV-UHFFFAOYSA-N 2-[3-[4-[(3,5-dimethylphenyl)methoxy]phenyl]-3-methyl-2-oxopyrrolidin-1-yl]-n-hydroxyacetamide Chemical compound CC1=CC(C)=CC(COC=2C=CC(=CC=2)C2(C)C(N(CC(=O)NO)CC2)=O)=C1 XIAUEHKDRHFIFV-UHFFFAOYSA-N 0.000 claims description 2
- OYHVFDKCIWIOGO-UHFFFAOYSA-N 2-[3-amino-3-[4-[(2,6-dimethylpyridin-4-yl)methoxy]phenyl]-2-oxopyrrolidin-1-yl]-n-hydroxy-3,3-dimethylbutanamide Chemical compound CC1=NC(C)=CC(COC=2C=CC(=CC=2)C2(N)C(N(C(C(=O)NO)C(C)(C)C)CC2)=O)=C1 OYHVFDKCIWIOGO-UHFFFAOYSA-N 0.000 claims description 2
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- 201000004792 malaria Diseases 0.000 description 1
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- DWKPPFQULDPWHX-GSVOUGTGSA-N methyl (2r)-2-aminopropanoate Chemical compound COC(=O)[C@@H](C)N DWKPPFQULDPWHX-GSVOUGTGSA-N 0.000 description 1
- CHSDCWKLSHPKFY-UHFFFAOYSA-N methyl 1-aminocyclopropane-1-carboxylate;hydrochloride Chemical compound [Cl-].COC(=O)C1([NH3+])CC1 CHSDCWKLSHPKFY-UHFFFAOYSA-N 0.000 description 1
- LGLSBOAKCKFRKY-UHFFFAOYSA-N methyl 2-(2-methyl-4-phenylmethoxyphenyl)acetate Chemical compound C1=C(C)C(CC(=O)OC)=CC=C1OCC1=CC=CC=C1 LGLSBOAKCKFRKY-UHFFFAOYSA-N 0.000 description 1
- HGJGPDQDXKDZTQ-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate Chemical compound CC(C)(C)OC(=O)NC(C(=O)OC)C1=CC=C(O)C=C1 HGJGPDQDXKDZTQ-UHFFFAOYSA-N 0.000 description 1
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- YNZYUHPFNYBBFF-UHFFFAOYSA-N methyl 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound COC(=O)C(C)C1=CC=C(CC(C)C)C=C1 YNZYUHPFNYBBFF-UHFFFAOYSA-N 0.000 description 1
- NVWZNEDLYYLQJC-UHFFFAOYSA-N methyl 2-amino-2-methylpropanoate;hydrochloride Chemical compound Cl.COC(=O)C(C)(C)N NVWZNEDLYYLQJC-UHFFFAOYSA-N 0.000 description 1
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- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 1
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- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 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
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- 235000009518 sodium iodide Nutrition 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 1
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
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- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/02—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
-
- 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
-
- 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
-
- 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
- C07D487/10—Spiro-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Virology (AREA)
- Cardiology (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
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- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US6241897P | 1997-10-03 | 1997-10-03 | |
PCT/US1998/021037 WO1999018074A1 (en) | 1997-10-03 | 1998-10-02 | Novel lactam metalloprotease inhibitors |
Publications (3)
Publication Number | Publication Date |
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NO20000783D0 NO20000783D0 (no) | 2000-02-17 |
NO20000783L NO20000783L (no) | 2000-05-29 |
NO315648B1 true NO315648B1 (no) | 2003-10-06 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20000783A NO315648B1 (no) | 1997-10-03 | 2000-02-17 | Nye metalloproteaseinhiberende laktamer, farmasöytisk preparat omfattende disse samt deres anvendelse for fremstilling av farmasöytiskepreparater |
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US (1) | US6057336A (ja) |
EP (1) | EP1027332B1 (ja) |
JP (1) | JP2001519331A (ja) |
KR (1) | KR20010015690A (ja) |
CN (1) | CN1272841A (ja) |
AR (1) | AR017291A1 (ja) |
AT (1) | ATE267805T1 (ja) |
AU (1) | AU747239B2 (ja) |
BR (1) | BR9815398A (ja) |
CA (1) | CA2305679A1 (ja) |
DE (1) | DE69824199T2 (ja) |
DK (1) | DK1027332T3 (ja) |
EE (1) | EE200000199A (ja) |
ES (1) | ES2217592T3 (ja) |
HR (1) | HRP980533A2 (ja) |
HU (1) | HUP0100186A3 (ja) |
IL (1) | IL135289A0 (ja) |
NO (1) | NO315648B1 (ja) |
NZ (1) | NZ504088A (ja) |
PL (1) | PL339738A1 (ja) |
PT (1) | PT1027332E (ja) |
SK (1) | SK4462000A3 (ja) |
TW (1) | TW541304B (ja) |
WO (1) | WO1999018074A1 (ja) |
ZA (1) | ZA988967B (ja) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
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US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
CA2361848A1 (en) | 1999-04-02 | 2000-10-12 | Dupont Pharmaceuticals Company | Novel lactam inhibitors of matrix metalloproteinases, tnf-.alpha., and aggrecanase |
AU4143300A (en) * | 1999-04-28 | 2000-11-17 | Takeda Chemical Industries Ltd. | Cyclic amide compounds, process for the preparation of the same and uses thereof |
MXPA01012322A (es) * | 1999-06-04 | 2002-07-22 | Astrazeneca Ab | Inhibidores de metaloproteinasas. |
US6656448B1 (en) * | 2000-02-15 | 2003-12-02 | Bristol-Myers Squibb Pharma Company | Matrix metalloproteinase inhibitors |
US6989139B2 (en) * | 2000-02-15 | 2006-01-24 | Bristol-Myers Squibb Pharma Company | Matrix metalloproteinase inhibitors |
US6620823B2 (en) | 2000-07-11 | 2003-09-16 | Bristol-Myers Squibb Pharme Company | Lactam metalloprotease inhibitors |
GB0119474D0 (en) * | 2001-08-09 | 2001-10-03 | Astrazeneca Ab | Compounds |
GB0127568D0 (en) | 2001-11-16 | 2002-01-09 | Glaxo Group Ltd | Chemical compounds |
PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
WO2003082287A1 (en) * | 2002-03-22 | 2003-10-09 | Bristol-Myers Squibb Company | Dpc 333 formulation having unique biopharmaceutical characteristics |
US20030225054A1 (en) * | 2002-06-03 | 2003-12-04 | Jingwu Duan | Combined use of tace inhibitors and COX2 inhibitors as anti-inflammatory agents |
US6770763B2 (en) * | 2002-06-11 | 2004-08-03 | Bristol-Myers Squibb Company | Asymmetric synthesis of amino-pyrrolidinones |
AU2003269801A1 (en) * | 2002-06-28 | 2004-01-19 | Bristol Myers Squibb Company | Asymmetric synthesis of amino-pyrrolidinones and a crystalline, free-base amino-pyrrolidinone |
US7199155B2 (en) | 2002-12-23 | 2007-04-03 | Wyeth Holdings Corporation | Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors |
SE0300445D0 (sv) * | 2003-02-18 | 2003-02-18 | Astrazeneca Ab | New combination |
SE0300480D0 (sv) | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
EP1663201A4 (en) * | 2003-07-15 | 2009-10-28 | Korea Res Inst Of Bioscience | USE OF NEW 2-OXO-HETEROCYCLIC COMPOUNDS AND PHARMACEUTICAL PREPARATIONS CONTAINING THEREOF |
JP4799408B2 (ja) * | 2003-07-15 | 2011-10-26 | コリア リサーチ インスティテュート オブ バイオサイエンス アンド バイオテクノロジー | 新規な2−オキソ複素環化合物およびそれを含有する薬剤組成物の使用 |
WO2005077937A1 (en) * | 2004-01-09 | 2005-08-25 | Cadila Healthcare Limited | Substituted hydroxamic acid derivatives as tnf inhibitors |
US20100226922A1 (en) * | 2006-06-08 | 2010-09-09 | Dorothea Maetzel | Specific protease inhibitors and their use in cancer therapy |
US9096565B2 (en) | 2007-04-09 | 2015-08-04 | Methylgene Inc. | Inhibitors of histone deacetylase |
WO2009094427A1 (en) | 2008-01-23 | 2009-07-30 | Bristol-Myers Squibb Company | 4-pyridinone compounds and their use for cancer |
DK2105164T3 (da) | 2008-03-25 | 2011-03-21 | Affectis Pharmaceuticals Ag | Nye P2X7R-antagonister og deres anvendelse |
JP5650642B2 (ja) * | 2008-08-01 | 2015-01-07 | バイオキシネス ファーマシューティカルズ, インコーポレイテッド | メチオニンアナログおよびそれらを使用する方法 |
RU2571662C2 (ru) | 2009-03-25 | 2015-12-20 | Эббви Инк. | Противовирусные соединения и их применения |
WO2010118921A1 (en) | 2009-04-14 | 2010-10-21 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
KR20140000689A (ko) * | 2010-10-08 | 2014-01-03 | 노파르티스 아게 | 술파미드 ns3 억제제의 염 및 다형체 |
WO2012077655A1 (ja) * | 2010-12-07 | 2012-06-14 | 塩野義製薬株式会社 | Gpr119アゴニスト活性を有するスピロ誘導体 |
WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
US20150023873A1 (en) | 2011-11-11 | 2015-01-22 | Lantheus Medical Imaging, Inc. | Evaluation of presence of and vulnerability to atrial fibrillation and other indications using matrix metalloproteinase-based imaging |
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US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US5318964A (en) * | 1992-06-11 | 1994-06-07 | Hoffmann-La Roche Inc. | Hydroxamic derivatives and pharmaceutical compositions |
GB9215665D0 (en) * | 1992-07-23 | 1992-09-09 | British Bio Technology | Compounds |
GB9307956D0 (en) * | 1993-04-17 | 1993-06-02 | Walls Alan J | Hydroxamic acid derivatives |
GB9320660D0 (en) * | 1993-10-07 | 1993-11-24 | British Bio Technology | Inhibition of cytokine production |
US5672598A (en) * | 1995-03-21 | 1997-09-30 | The Procter & Gamble Company | Lactam-containing hydroxamic acids |
AU7604196A (en) * | 1995-10-30 | 1997-05-22 | Merck & Co., Inc. | Novel inhibitors of peptide binding to mhc class ii proteins |
TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
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1998
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- 1998-10-02 KR KR1020007003563A patent/KR20010015690A/ko not_active Application Discontinuation
- 1998-10-02 AT AT98950954T patent/ATE267805T1/de not_active IP Right Cessation
- 1998-10-02 CN CN98809703A patent/CN1272841A/zh active Pending
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- 1998-10-02 NZ NZ504088A patent/NZ504088A/en unknown
- 1998-10-02 EP EP98950954A patent/EP1027332B1/en not_active Expired - Lifetime
- 1998-10-02 PT PT98950954T patent/PT1027332E/pt unknown
- 1998-10-02 BR BR9815398-6A patent/BR9815398A/pt not_active IP Right Cessation
- 1998-10-02 SK SK446-2000A patent/SK4462000A3/sk unknown
- 1998-10-02 US US09/165,747 patent/US6057336A/en not_active Expired - Lifetime
- 1998-10-02 IL IL13528998A patent/IL135289A0/xx unknown
- 1998-10-02 HU HU0100186A patent/HUP0100186A3/hu unknown
- 1998-10-02 PL PL98339738A patent/PL339738A1/xx unknown
- 1998-10-02 DE DE69824199T patent/DE69824199T2/de not_active Expired - Lifetime
- 1998-10-02 EE EEP200000199A patent/EE200000199A/xx unknown
- 1998-10-02 JP JP2000514886A patent/JP2001519331A/ja not_active Withdrawn
- 1998-10-02 WO PCT/US1998/021037 patent/WO1999018074A1/en not_active Application Discontinuation
- 1998-10-02 CA CA002305679A patent/CA2305679A1/en not_active Abandoned
- 1998-10-02 AR ARP980104945A patent/AR017291A1/es not_active Application Discontinuation
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- 1998-10-02 ES ES98950954T patent/ES2217592T3/es not_active Expired - Lifetime
- 1998-10-21 TW TW087116499A patent/TW541304B/zh active
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2000
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Also Published As
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DK1027332T3 (da) | 2004-10-04 |
EP1027332A1 (en) | 2000-08-16 |
EE200000199A (et) | 2001-04-16 |
AR017291A1 (es) | 2001-09-05 |
HRP980533A2 (en) | 1999-10-31 |
EP1027332B1 (en) | 2004-05-26 |
US6057336A (en) | 2000-05-02 |
DE69824199D1 (de) | 2004-07-01 |
AU9686698A (en) | 1999-04-27 |
CN1272841A (zh) | 2000-11-08 |
SK4462000A3 (en) | 2002-06-04 |
JP2001519331A (ja) | 2001-10-23 |
HUP0100186A2 (hu) | 2001-05-28 |
ES2217592T3 (es) | 2004-11-01 |
NO20000783D0 (no) | 2000-02-17 |
ATE267805T1 (de) | 2004-06-15 |
DE69824199T2 (de) | 2005-01-27 |
PT1027332E (pt) | 2004-08-31 |
NO20000783L (no) | 2000-05-29 |
PL339738A1 (en) | 2001-01-02 |
HUP0100186A3 (en) | 2002-12-28 |
ZA988967B (en) | 2000-04-03 |
BR9815398A (pt) | 2000-10-31 |
IL135289A0 (en) | 2001-05-20 |
WO1999018074A1 (en) | 1999-04-15 |
NZ504088A (en) | 2001-09-28 |
TW541304B (en) | 2003-07-11 |
AU747239B2 (en) | 2002-05-09 |
KR20010015690A (ko) | 2001-02-26 |
CA2305679A1 (en) | 1999-04-15 |
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