NO971687L - Diazepinoindoler som forsfodiesterase IV-inhibitorer - Google Patents
Diazepinoindoler som forsfodiesterase IV-inhibitorerInfo
- Publication number
- NO971687L NO971687L NO971687A NO971687A NO971687L NO 971687 L NO971687 L NO 971687L NO 971687 A NO971687 A NO 971687A NO 971687 A NO971687 A NO 971687A NO 971687 L NO971687 L NO 971687L
- Authority
- NO
- Norway
- Prior art keywords
- yield
- tlc
- phenyl
- ppm
- acid
- Prior art date
Links
- BSYFXFLGOGQHFU-UHFFFAOYSA-N pyrrolo[2,3-g][1,2]benzodiazepine Chemical class N1=NC=CC=C2C3=NC=CC3=CC=C21 BSYFXFLGOGQHFU-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title claims description 14
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title claims description 5
- -1 2-indolyl Chemical group 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- QVPUISMYRDHJMF-UHFFFAOYSA-N O=C1C=C2N=NC=CC=C2C2=C1C=CN2 Chemical group O=C1C=C2N=NC=CC=C2C2=C1C=CN2 QVPUISMYRDHJMF-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 119
- 150000001875 compounds Chemical class 0.000 abstract description 107
- 230000000694 effects Effects 0.000 abstract description 15
- 101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
- 238000004809 thin layer chromatography Methods 0.000 description 91
- 239000000543 intermediate Substances 0.000 description 83
- 238000005481 NMR spectroscopy Methods 0.000 description 76
- 238000004458 analytical method Methods 0.000 description 73
- 239000007787 solid Substances 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000460 chlorine Substances 0.000 description 56
- 239000000047 product Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- 239000000203 mixture Substances 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
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- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 15
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 8
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- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 210000000224 granular leucocyte Anatomy 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- KCKIKSJECTZLJA-UHFFFAOYSA-N indol-4-one Chemical compound O=C1C=CC=C2N=CC=C12 KCKIKSJECTZLJA-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- JFCXJLMOHOXSTO-UHFFFAOYSA-N 4,7-dimethylpyrazolo[5,1-c][1,2,4]triazine-3-carboxylic acid Chemical compound N1=NC(C(O)=O)=C(C)N2N=C(C)C=C21 JFCXJLMOHOXSTO-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 108090000695 Cytokines Proteins 0.000 description 3
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- CBQJSKKFNMDLON-JTQLQIEISA-N N-acetyl-L-phenylalanine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- SEKHCAFZRYHQMP-UHFFFAOYSA-N quinoline-6-carbonyl chloride Chemical compound N1=CC=CC2=CC(C(=O)Cl)=CC=C21 SEKHCAFZRYHQMP-UHFFFAOYSA-N 0.000 description 1
- VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- WNAHEVXTGAEKIY-ZDUSSCGKSA-N tert-butyl n-[(2r)-1-phenylbut-3-en-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C=C)CC1=CC=CC=C1 WNAHEVXTGAEKIY-ZDUSSCGKSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- C07D487/06—Peri-condensed systems
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
-
- 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
-
- 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
- A61P11/08—Bronchodilators
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9412282A FR2725719B1 (fr) | 1994-10-14 | 1994-10-14 | Diazepino-indoles inhibiteurs de phosphodiesterases iv |
| PCT/FR1995/001354 WO1996011690A1 (fr) | 1994-10-14 | 1995-10-13 | Diazepino-indoles inhibiteurs de phosphodiesterases iv |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO971687D0 NO971687D0 (no) | 1997-04-11 |
| NO971687L true NO971687L (no) | 1997-06-13 |
Family
ID=9467863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO971687A NO971687L (no) | 1994-10-14 | 1997-04-11 | Diazepinoindoler som forsfodiesterase IV-inhibitorer |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5852190A (de) |
| EP (1) | EP0785789B1 (de) |
| JP (1) | JPH10507447A (de) |
| KR (1) | KR970706826A (de) |
| CN (1) | CN1097459C (de) |
| AT (1) | ATE223720T1 (de) |
| AU (1) | AU703773B2 (de) |
| BR (1) | BR9509353A (de) |
| CA (1) | CA2200628A1 (de) |
| CZ (1) | CZ111497A3 (de) |
| DE (1) | DE69528189T2 (de) |
| DK (1) | DK0785789T3 (de) |
| ES (1) | ES2181793T3 (de) |
| FR (1) | FR2725719B1 (de) |
| HU (1) | HUT77411A (de) |
| NO (1) | NO971687L (de) |
| NZ (1) | NZ294642A (de) |
| PL (1) | PL319659A1 (de) |
| PT (1) | PT785789E (de) |
| RU (1) | RU2174517C2 (de) |
| SK (1) | SK282766B6 (de) |
| UA (1) | UA42793C2 (de) |
| WO (1) | WO1996011690A1 (de) |
| ZA (1) | ZA958669B (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2746800B1 (fr) * | 1996-03-29 | 1998-06-05 | Jouveinal Inst Rech | Diazepino-indoles inhibiteurs de phosphodiesterases 4 |
| FR2762841B1 (fr) * | 1997-04-30 | 1999-07-02 | Jouveinal Inst Rech | Diazepino-indolones inhibitrices de phosphodiesterases iv |
| FR2776660B1 (fr) * | 1998-03-27 | 2000-05-12 | Parke Davis | Diazepino-indoles de phosphodiesterases iv |
| TR200909479T2 (tr) | 1999-08-21 | 2012-02-21 | Nycomed Gmbh | Sinerjistik kombinasyon. |
| CA2395772C (en) | 1999-12-28 | 2010-09-28 | Eisai Co., Ltd. | Sulfonamide-containing heterocyclic compounds |
| WO2001064669A1 (en) * | 2000-03-03 | 2001-09-07 | Pfizer Products Inc. | Pyrazole ether derivatives as anti-inflammatory/analgesic agents |
| EP1161949A1 (de) | 2000-06-09 | 2001-12-12 | Warner-Lambert Company | Verwendung von diazepinoindolen zur behandlung von chronisch obstruktiver lungenkrankheiten |
| EP1188438A1 (de) * | 2000-09-15 | 2002-03-20 | Warner-Lambert Company | Pharmazeutische Zusammensetzungen zur Vorbeugung oder Behandlung von mit IL-12 Überproduktion assozierten Erkrankungen |
| EP1199074A1 (de) * | 2000-09-15 | 2002-04-24 | Warner-Lambert Company | Pharmazeutische Zusammensetzungen zur Vorbeugung oder Behandlung von mit IL-12 Überproduktion assozierten Erkrankungen |
| DE10148290A1 (de) * | 2001-09-29 | 2003-04-17 | Bayer Cropscience Gmbh | Heterocyclische Amide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung |
| WO2006040645A1 (en) * | 2004-10-11 | 2006-04-20 | Ranbaxy Laboratories Limited | N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma |
| EP3165224A1 (de) | 2015-11-09 | 2017-05-10 | Albert-Ludwigs-Universität Freiburg | Verwendung von pde4 hemmern zur prophylaxe und/oder therapie von dyslipoproteinaemie und verwandten erkrankungen |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4840947A (en) * | 1986-10-14 | 1989-06-20 | Hoechst-Roussel Pharmaceuticals, Inc. | Antiinflammatory and analgesic piperidin-4-yl-tetracyclic benzodiazepines and use thereas |
| FR2630440B1 (fr) * | 1988-04-25 | 1991-09-20 | Jouveinal Sa | Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique |
| US5248679A (en) * | 1988-09-09 | 1993-09-28 | Fujisawa Pharmaceutical Co., Ltd. | Tricyclic compounds |
| IL91361A (en) * | 1988-09-09 | 1994-10-07 | Fujisawa Pharmaceutical Co | Benzodiazepinone compounds [4,1] connected via positions 1 and 9 and carrying two transducers, processes for their preparation and pharmaceutical preparations containing them |
| FR2652352A1 (fr) * | 1989-09-28 | 1991-03-29 | Jouveinal Sa | Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique. |
-
1994
- 1994-10-14 FR FR9412282A patent/FR2725719B1/fr not_active Expired - Fee Related
-
1995
- 1995-02-22 US US08/391,865 patent/US5852190A/en not_active Expired - Fee Related
- 1995-10-13 CN CN95195634A patent/CN1097459C/zh not_active Expired - Fee Related
- 1995-10-13 CZ CZ971114A patent/CZ111497A3/cs unknown
- 1995-10-13 DE DE69528189T patent/DE69528189T2/de not_active Expired - Fee Related
- 1995-10-13 WO PCT/FR1995/001354 patent/WO1996011690A1/fr not_active Application Discontinuation
- 1995-10-13 EP EP95935495A patent/EP0785789B1/de not_active Expired - Lifetime
- 1995-10-13 HU HU9702065A patent/HUT77411A/hu unknown
- 1995-10-13 RU RU97108048/14A patent/RU2174517C2/ru not_active IP Right Cessation
- 1995-10-13 PL PL95319659A patent/PL319659A1/xx unknown
- 1995-10-13 AU AU37494/95A patent/AU703773B2/en not_active Ceased
- 1995-10-13 ES ES95935495T patent/ES2181793T3/es not_active Expired - Lifetime
- 1995-10-13 CA CA002200628A patent/CA2200628A1/fr not_active Abandoned
- 1995-10-13 KR KR1019970702405A patent/KR970706826A/ko active IP Right Grant
- 1995-10-13 PT PT95935495T patent/PT785789E/pt unknown
- 1995-10-13 BR BR9509353A patent/BR9509353A/pt not_active Application Discontinuation
- 1995-10-13 DK DK95935495T patent/DK0785789T3/da active
- 1995-10-13 AT AT95935495T patent/ATE223720T1/de not_active IP Right Cessation
- 1995-10-13 SK SK448-97A patent/SK282766B6/sk unknown
- 1995-10-13 JP JP8512999A patent/JPH10507447A/ja not_active Withdrawn
- 1995-10-13 ZA ZA958669A patent/ZA958669B/xx unknown
- 1995-10-13 UA UA97052184A patent/UA42793C2/uk unknown
-
1997
- 1997-04-11 NO NO971687A patent/NO971687L/no not_active Application Discontinuation
- 1997-04-14 NZ NZ294642A patent/NZ294642A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE223720T1 (de) | 2002-09-15 |
| EP0785789A1 (de) | 1997-07-30 |
| ZA958669B (en) | 1997-04-14 |
| RU2174517C2 (ru) | 2001-10-10 |
| NO971687D0 (no) | 1997-04-11 |
| UA42793C2 (uk) | 2001-11-15 |
| FR2725719A1 (fr) | 1996-04-19 |
| PT785789E (pt) | 2002-12-31 |
| ES2181793T3 (es) | 2003-03-01 |
| DE69528189T2 (de) | 2003-01-09 |
| SK282766B6 (sk) | 2002-12-03 |
| BR9509353A (pt) | 1997-12-30 |
| DE69528189D1 (de) | 2002-10-17 |
| AU703773B2 (en) | 1999-04-01 |
| FR2725719B1 (fr) | 1996-12-06 |
| CN1160352A (zh) | 1997-09-24 |
| AU3749495A (en) | 1996-05-06 |
| WO1996011690A1 (fr) | 1996-04-25 |
| CZ111497A3 (cs) | 1998-01-14 |
| US5852190A (en) | 1998-12-22 |
| CN1097459C (zh) | 2003-01-01 |
| KR970706826A (ko) | 1997-12-01 |
| DK0785789T3 (da) | 2003-01-20 |
| SK44897A3 (en) | 1998-12-02 |
| JPH10507447A (ja) | 1998-07-21 |
| MX9702637A (es) | 1997-07-31 |
| EP0785789B1 (de) | 2002-09-11 |
| HUT77411A (hu) | 1998-04-28 |
| CA2200628A1 (fr) | 1996-04-25 |
| PL319659A1 (en) | 1997-08-18 |
| NZ294642A (en) | 2001-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application |