ZA200504387B - Aromatic compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents. - Google Patents
Aromatic compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents. Download PDFInfo
- Publication number
- ZA200504387B ZA200504387B ZA200504387A ZA200504387A ZA200504387B ZA 200504387 B ZA200504387 B ZA 200504387B ZA 200504387 A ZA200504387 A ZA 200504387A ZA 200504387 A ZA200504387 A ZA 200504387A ZA 200504387 B ZA200504387 B ZA 200504387B
- Authority
- ZA
- South Africa
- Prior art keywords
- carboxylic acid
- thiophene
- alkyl
- aryl
- cycloalkyl
- Prior art date
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- CMSCIKGPPSZJCR-UHFFFAOYSA-N 4-[(4-naphthalen-2-yl-1,3-thiazol-2-yl)carbamoyl]furan-3-carboxylic acid Chemical compound OC(=O)C1=COC=C1C(=O)NC1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 CMSCIKGPPSZJCR-UHFFFAOYSA-N 0.000 claims description 2
- IGZXVCCGRAIYSA-UHFFFAOYSA-N 5-[(4-naphthalen-2-yl-1,3-thiazol-2-yl)carbamoyl]-2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=NNN=C1C(=O)NC1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 IGZXVCCGRAIYSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
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- QUZTWSMTEVXSPF-UHFFFAOYSA-N 2-(tert-butylcarbamoyl)thiophene-3-carboxylic acid Chemical compound CC(C)(C)NC(=O)C=1SC=CC=1C(O)=O QUZTWSMTEVXSPF-UHFFFAOYSA-N 0.000 claims 3
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims 3
- NZOLKIUOTPQVOQ-UHFFFAOYSA-N 3-(propan-2-ylcarbamoyl)thiophene-2-carboxylic acid Chemical compound CC(C)NC(=O)C=1C=CSC=1C(O)=O NZOLKIUOTPQVOQ-UHFFFAOYSA-N 0.000 claims 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims 2
- IACYWQZBPYYSMB-UHFFFAOYSA-N 2-(dimethylcarbamoyl)thiophene-3-carboxylic acid Chemical compound CN(C)C(=O)C=1SC=CC=1C(O)=O IACYWQZBPYYSMB-UHFFFAOYSA-N 0.000 claims 1
- LNOOSIAAAWRNAD-UHFFFAOYSA-N 2-(ethylcarbamoyl)thiophene-3-carboxylic acid Chemical compound CCNC(=O)C=1SC=CC=1C(O)=O LNOOSIAAAWRNAD-UHFFFAOYSA-N 0.000 claims 1
- HGZGDMAYBFUUFW-UHFFFAOYSA-N 2-(phenylcarbamoyl)furan-3-carboxylic acid Chemical compound C1=COC(C(=O)NC=2C=CC=CC=2)=C1C(=O)O HGZGDMAYBFUUFW-UHFFFAOYSA-N 0.000 claims 1
- CYYDCXXRPAYVGR-UHFFFAOYSA-N 2-(phenylcarbamoyl)thiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC=2C=CC=CC=2)=C1C(=O)O CYYDCXXRPAYVGR-UHFFFAOYSA-N 0.000 claims 1
- YTKRFDCFPYKBHO-UHFFFAOYSA-N 2-(propan-2-ylcarbamoyl)furan-3-carboxylic acid Chemical compound CC(C)NC(=O)C=1OC=CC=1C(O)=O YTKRFDCFPYKBHO-UHFFFAOYSA-N 0.000 claims 1
- GWZMIBAGTLDOFN-UHFFFAOYSA-N 2-(tert-butylcarbamoyl)furan-3-carboxylic acid Chemical compound CC(C)(C)NC(=O)C=1OC=CC=1C(O)=O GWZMIBAGTLDOFN-UHFFFAOYSA-N 0.000 claims 1
- IAVZZEMLMOEQOK-UHFFFAOYSA-N 2-[(2,5-dibromothiophen-3-yl)carbamoyl]thiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC2=C(SC(Br)=C2)Br)=C1C(=O)O IAVZZEMLMOEQOK-UHFFFAOYSA-N 0.000 claims 1
- QFHMYSHYSGYAFC-UHFFFAOYSA-N 2-[(2,5-dichlorothiophen-3-yl)carbamoyl]thiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC2=C(SC(Cl)=C2)Cl)=C1C(=O)O QFHMYSHYSGYAFC-UHFFFAOYSA-N 0.000 claims 1
- PSASPXQXYYWSDW-UHFFFAOYSA-N 2-[(4-chlorophenyl)carbamoyl]thiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC=2C=CC(Cl)=CC=2)=C1C(=O)O PSASPXQXYYWSDW-UHFFFAOYSA-N 0.000 claims 1
- RAQNAMMQJITSHO-UHFFFAOYSA-N 2-[[3-(trifluoromethyl)phenyl]carbamoyl]thiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1C(=O)O RAQNAMMQJITSHO-UHFFFAOYSA-N 0.000 claims 1
- ATAXWINYVVWLPZ-UHFFFAOYSA-N 2-[methyl(phenyl)carbamoyl]thiophene-3-carboxylic acid Chemical compound C=1C=CC=CC=1N(C)C(=O)C=1SC=CC=1C(O)=O ATAXWINYVVWLPZ-UHFFFAOYSA-N 0.000 claims 1
- GRFOHUBBUMAJMM-UHFFFAOYSA-N 3-(2-aminoquinolin-3-yl)-n-cyclohexyl-n-methylpropanamide Chemical compound C=1C2=CC=CC=C2N=C(N)C=1CCC(=O)N(C)C1CCCCC1 GRFOHUBBUMAJMM-UHFFFAOYSA-N 0.000 claims 1
- GHMNNOGAAQKJOJ-UHFFFAOYSA-N 3-(phenylcarbamoyl)thiophene-2-carboxylic acid Chemical compound S1C=CC(C(=O)NC=2C=CC=CC=2)=C1C(=O)O GHMNNOGAAQKJOJ-UHFFFAOYSA-N 0.000 claims 1
- LSUJLRQVWMDYLD-UHFFFAOYSA-N 3-(tert-butylcarbamoyl)thiophene-2-carboxylic acid Chemical compound CC(C)(C)NC(=O)C=1C=CSC=1C(O)=O LSUJLRQVWMDYLD-UHFFFAOYSA-N 0.000 claims 1
- PFSKFXIVPBLBJE-UHFFFAOYSA-N 3-[methyl(phenyl)carbamoyl]thiophene-2-carboxylic acid Chemical compound C=1C=CC=CC=1N(C)C(=O)C=1C=CSC=1C(O)=O PFSKFXIVPBLBJE-UHFFFAOYSA-N 0.000 claims 1
- RUNMORKVPCSMTK-UHFFFAOYSA-N 3-formylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1C=O RUNMORKVPCSMTK-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010061217 Infestation Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 241000233872 Pneumocystis carinii Species 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
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- OLYIHCXRYTVESD-UHFFFAOYSA-N methyl 2-[methyl(phenyl)carbamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(C(=O)N(C)C=2C=CC=CC=2)=C1C(=O)OC OLYIHCXRYTVESD-UHFFFAOYSA-N 0.000 claims 1
- HNJDJDFZVGHLOY-UHFFFAOYSA-N methyl 3-[methyl(phenyl)carbamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(C(=O)N(C)C=2C=CC=CC=2)=C1C(=O)OC HNJDJDFZVGHLOY-UHFFFAOYSA-N 0.000 claims 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FSEUPUDHEBLWJY-UHFFFAOYSA-N diacetylmonoxime Chemical class CC(=O)C(C)=NO FSEUPUDHEBLWJY-UHFFFAOYSA-N 0.000 description 1
- JWLIWPUUZTZGLA-UHFFFAOYSA-N diethyl 4-acetyl-5-methylfuran-2,3-dicarboxylate Chemical compound CCOC(=O)C=1OC(C)=C(C(C)=O)C=1C(=O)OCC JWLIWPUUZTZGLA-UHFFFAOYSA-N 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
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- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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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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- A61P11/02—Nasal agents, e.g. decongestants
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- 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
- A61P11/06—Antiasthmatics
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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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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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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- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
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- 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]
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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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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Otolaryngology (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10260800 | 2002-12-23 |
Publications (1)
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| ZA200504387B true ZA200504387B (en) | 2006-02-22 |
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| ZA200504387A ZA200504387B (en) | 2002-12-23 | 2005-05-30 | Aromatic compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents. |
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| JP (3) | JP2006514023A (fr) |
| KR (1) | KR101107456B1 (fr) |
| CN (3) | CN1732147A (fr) |
| AT (2) | ATE450498T1 (fr) |
| AU (2) | AU2003299316A1 (fr) |
| BR (2) | BR0317731A (fr) |
| CA (2) | CA2509138A1 (fr) |
| CY (1) | CY1111851T1 (fr) |
| DE (1) | DE60330391D1 (fr) |
| DK (1) | DK1578741T3 (fr) |
| ES (1) | ES2368735T3 (fr) |
| IL (2) | IL169184A (fr) |
| MX (2) | MXPA05006889A (fr) |
| NO (2) | NO20052907L (fr) |
| NZ (1) | NZ541382A (fr) |
| PL (2) | PL209303B1 (fr) |
| PT (1) | PT1578741E (fr) |
| RU (2) | RU2367650C2 (fr) |
| SI (1) | SI1578741T1 (fr) |
| WO (1) | WO2004056797A1 (fr) |
| ZA (1) | ZA200504387B (fr) |
Families Citing this family (11)
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| AU2009313053A1 (en) * | 2008-11-07 | 2010-05-14 | 4Sc Ag | Combinational therapy comprising DHODH inhibitor and methotrexate for treating autoimmune disease |
| TWI530286B (zh) * | 2009-05-04 | 2016-04-21 | 帕納特斯製藥格斯有限公司 | 作為抑制病毒化合物之抗發炎劑 |
| US8686048B2 (en) | 2010-05-06 | 2014-04-01 | Rhizen Pharmaceuticals Sa | Immunomodulator and anti-inflammatory compounds |
| US20140031383A1 (en) | 2011-02-08 | 2014-01-30 | Dana-Farber Cancer Institute, Inc. | Methods for treatment of melanoma |
| RU2485112C1 (ru) * | 2012-04-26 | 2013-06-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 4-(4-бромфенил)-4-оксо-2-{[3-(этоксикарбонил)-4,5-диметилтиен-2-ил]амино}-2-бутеновая кислота, обладающая противовоспалительной и анальгетической активностью |
| JP6271806B2 (ja) * | 2014-04-11 | 2018-01-31 | パノプテス・ファーマ・ゲーエムベーハー | ウイルス静止化合物としての抗炎症剤 |
| CA2947067C (fr) * | 2014-05-08 | 2023-02-14 | Panoptes Pharma Ges.M.B.H. | Composes pour le traitement de maladies et troubles ophtalmiques |
| JP2020504711A (ja) | 2016-12-21 | 2020-02-13 | バイオセリックス， インコーポレイテッド | タンパク質を標的とすることにおいて使用するための、チエノピロール誘導体、その組成物、方法、および使用 |
| WO2022167402A1 (fr) | 2021-02-02 | 2022-08-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés thérapeutiques comprenant l'administration d'une association thérapeutiquement efficace comprenant un inhibiteur de dhodh et un inhibiteur d'idh |
| US20240199535A1 (en) | 2021-04-09 | 2024-06-20 | Immunic Ag | Deuterated dhodh inhibitors |
| AU2022422334A1 (en) | 2021-12-23 | 2024-06-13 | Immunic Ag | Dhodh inhibitors containing a carboxylic acid bioisostere |
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| NL186239B (nl) | 1975-06-05 | Hoechst Ag | Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze. | |
| AU1526483A (en) * | 1982-06-14 | 1983-12-22 | Nippon Kayaku Kabushiki Kaisha | N-substituted-3,4,5,6-tetrahydrophthalamic acids |
| ZA839187B (en) * | 1982-12-10 | 1984-07-25 | Ciba Geigy Ag | Amide compounds |
| GB8311519D0 (en) * | 1983-04-27 | 1983-06-02 | Fisons Plc | Nitrogen heterocycles |
| GB8323293D0 (en) * | 1983-08-31 | 1983-10-05 | Zyma Sa | Substituted flavene and thioflavene derivatives |
| DE3402026A1 (de) | 1984-01-21 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | Neue 2-aminothiophenderivate |
| DE3534440A1 (de) | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
| DE3812225A1 (de) * | 1988-04-13 | 1989-10-26 | Basf Ag | Isoxazol(isothiazol)-5-carbonsaeureamide |
| DE59009528D1 (de) * | 1989-09-22 | 1995-09-21 | Basf Ag | Carbonsäureamide. |
| DE3932052A1 (de) * | 1989-09-26 | 1991-04-04 | Basf Ag | Oxazol- bzw. thiazolcarbonsaeureamide |
| DE3933573A1 (de) | 1989-10-07 | 1991-04-18 | Basf Ag | Carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE59106349D1 (de) | 1990-06-23 | 1995-10-05 | Basf Ag | Dicarbonsäureimide als Herbizide. |
| DE4023048A1 (de) * | 1990-07-20 | 1992-01-23 | Basf Ag | Dicarbonsaeureimide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE4108181A1 (de) * | 1991-03-14 | 1992-09-17 | Basf Ag | Isoxazol- und isothiazol-5-carbonsaeureamide |
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2003
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