NO311222B1 - Ortokondenserte pyrrolderivater, farmasöytiske preparater som inneholder disse, anvendelse av forbindelsene for fremstilling avfarmasöytiske preparater, og mellomprodukter for fremstilling avforbindelsene - Google Patents

Ortokondenserte pyrrolderivater, farmasöytiske preparater som inneholder disse, anvendelse av forbindelsene for fremstilling avfarmasöytiske preparater, og mellomprodukter for fremstilling avforbindelsene Download PDF

Info

Publication number: NO311222B1
Authority: NO; Norway
Prior art keywords: stands; phenyl; compounds; formula; chlorophenyl
Prior art date: 1994-06-01

Application number

NO19965094A

Other languages

English (en)

Norwegian (no)

Other versions

NO965094L (no

NO965094D0 (no

Inventor

Stefan Laufer

Hans Guenther Striegel

Gerd Dannhardt

Original Assignee

Merckle Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-06-01

Filing date

1996-11-29

Publication date

2001-10-29

1996-11-29 Application filed by Merckle Gmbh filed Critical Merckle Gmbh

1996-11-29 Publication of NO965094D0 publication Critical patent/NO965094D0/no

1996-12-11 Publication of NO965094L publication Critical patent/NO965094L/no

2001-10-29 Publication of NO311222B1 publication Critical patent/NO311222B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 69
239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
150000003233 pyrroles Chemical class 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 13
239000008194 pharmaceutical composition Substances 0.000 title 1
239000012450 pharmaceutical intermediate Substances 0.000 title 1
201000010099 disease Diseases 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
238000011282 treatment Methods 0.000 claims abstract description 6
208000025747 Rheumatic disease Diseases 0.000 claims abstract description 5
230000002265 prevention Effects 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 12
-1 5-chloro-2-thienyl Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 7
230000000172 allergic effect Effects 0.000 claims description 6
208000010668 atopic eczema Diseases 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
239000000543 intermediate Substances 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
229930192474 thiophene Natural products 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
230000000552 rheumatic effect Effects 0.000 abstract 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
238000000034 method Methods 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
238000005481 NMR spectroscopy Methods 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
239000000243 solution Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
238000002329 infrared spectrum Methods 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 6
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000012071 phase Substances 0.000 description 6
JXLGIKDMRFJFHY-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-phenyl-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 JXLGIKDMRFJFHY-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
229940114079 arachidonic acid Drugs 0.000 description 5
235000021342 arachidonic acid Nutrition 0.000 description 5
238000009835 boiling Methods 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
PPNSEQJNDMLOMT-UHFFFAOYSA-N 2-[7-(4-chlorophenyl)-3,3-dimethyl-8-phenyl-2,4-dihydropyrrolo[2,1-b][1,3]thiazin-6-yl]acetic acid Chemical compound OC(=O)CC=1N2CC(C)(C)CSC2=C(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 PPNSEQJNDMLOMT-UHFFFAOYSA-N 0.000 description 4
KWKYBQVUEUNCCY-QGZVFWFLSA-N 3-(4-chlorophenyl)-1-[(2r)-2-hydroxybutyl]-4-phenyl-2h-pyrrol-5-one Chemical compound O=C1N(C[C@H](O)CC)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=CC=C1 KWKYBQVUEUNCCY-QGZVFWFLSA-N 0.000 description 4
YPMJGMXAYABHNX-UHFFFAOYSA-N 7-(4-chlorophenyl)-3,3-dimethyl-8-phenyl-2,4-dihydropyrrolo[2,1-b][1,3]thiazine Chemical compound C=1N2CC(C)(C)CSC2=C(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 YPMJGMXAYABHNX-UHFFFAOYSA-N 0.000 description 4
102000003820 Lipoxygenases Human genes 0.000 description 4
108090000128 Lipoxygenases Proteins 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
150000003462 sulfoxides Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YOSCSFCHAKAHDF-UHFFFAOYSA-N 2-benzyl-4-methyl-1,3-thiazole Chemical compound CC1=CSC(CC=2C=CC=CC=2)=N1 YOSCSFCHAKAHDF-UHFFFAOYSA-N 0.000 description 3
CHCRPRMXPJACLD-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-4-phenyl-2h-pyrrol-5-one Chemical compound O=C1N(CC(C)(CO)C)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=CC=C1 CHCRPRMXPJACLD-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
ZDRBVLIJSBGYGF-UHFFFAOYSA-N ethyl 2-[7-(4-chlorophenyl)-3,3-dimethyl-8-phenyl-2,4-dihydropyrrolo[2,1-b][1,3]thiazin-6-yl]-2-oxoacetate Chemical compound C=12SCC(C)(C)CN2C(C(=O)C(=O)OCC)=C(C=2C=CC(Cl)=CC=2)C=1C1=CC=CC=C1 ZDRBVLIJSBGYGF-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
230000037361 pathway Effects 0.000 description 3
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
150000003180 prostaglandins Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003457 sulfones Chemical class 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
AQMZKZUPLHKJHI-UHFFFAOYSA-N 2-[6-(5-chlorothiophen-2-yl)-3-methyl-7-phenylpyrrolo[2,1-b][1,3]thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1N2C(C)=CSC2=C(C=2C=CC=CC=2)C=1C1=CC=C(Cl)S1 AQMZKZUPLHKJHI-UHFFFAOYSA-N 0.000 description 2
CPBAHTZRJQATEJ-UHFFFAOYSA-N 3,4-diphenyl-2h-furan-5-one Chemical compound O=C1OCC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPBAHTZRJQATEJ-UHFFFAOYSA-N 0.000 description 2
FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
JJNHODVCSWJNQW-UHFFFAOYSA-N 6-(4-chlorophenyl)-3,3-dimethyl-7-phenyl-2h-pyrrolo[2,1-b][1,3]thiazole Chemical compound C=1N2C(C)(C)CSC2=C(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 JJNHODVCSWJNQW-UHFFFAOYSA-N 0.000 description 2
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RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000007257 deesterification reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
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238000004508 fractional distillation Methods 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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DGQDXWODJFYOGI-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-phenylpropanamide Chemical compound OCCCNC(=O)C(C)C1=CC=CC=C1 DGQDXWODJFYOGI-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
150000003238 pyrrolizines Chemical class 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
239000006188 syrup Substances 0.000 description 2
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RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
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239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000007395 thrombosis prophylaxis Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910001845 yogo sapphire Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61P17/00—Drugs for dermatological disorders
- 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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
- A—HUMAN NECESSITIES
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- 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
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical 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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Dermatology (AREA)
Biomedical Technology (AREA)
Oncology (AREA)
Rheumatology (AREA)
Immunology (AREA)
Neurology (AREA)
Communicable Diseases (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO19965094A 1994-06-01 1996-11-29 Ortokondenserte pyrrolderivater, farmasöytiske preparater som inneholder disse, anvendelse av forbindelsene for fremstilling avfarmasöytiske preparater, og mellomprodukter for fremstilling avforbindelsene NO311222B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4419315A DE4419315A1 (de)	1994-06-01	1994-06-01	Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie
PCT/EP1995/002078 WO1995032971A1 (de)	1994-06-01	1995-05-31	[a]-ANNELIERTE PYRROLDERIVATE UND DEREN ANWENDUNG IN DER PHARMAZIE

Publications (3)

Publication Number	Publication Date
NO965094D0 NO965094D0 (no)	1996-11-29
NO965094L NO965094L (no)	1996-12-11
NO311222B1 true NO311222B1 (no)	2001-10-29

Family

ID=6519632

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19965094A NO311222B1 (no)	1994-06-01	1996-11-29	Ortokondenserte pyrrolderivater, farmasöytiske preparater som inneholder disse, anvendelse av forbindelsene for fremstilling avfarmasöytiske preparater, og mellomprodukter for fremstilling avforbindelsene

Country Status (13)

Country	Link
US (1)	US5939415A (da)
EP (1)	EP0804437B1 (da)
JP (1)	JP3569823B2 (da)
KR (1)	KR100378882B1 (da)
AT (1)	ATE304543T1 (da)
AU (1)	AU2672995A (da)
CA (1)	CA2191745A1 (da)
DE (2)	DE4419315A1 (da)
DK (1)	DK0804437T3 (da)
ES (1)	ES2248798T3 (da)
FI (1)	FI113966B (da)
NO (1)	NO311222B1 (da)
WO (1)	WO1995032971A1 (da)

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DE10004157A1 (de)	2000-02-01	2001-08-02	Merckle Gmbh Chem Pharm Fabrik	4-Pyridyl-und 2,4-Pyrimidinyl-substituierte Pyrrolderivate und ihre Anwendung in der Pharmazie
DE10141285A1 (de)	2001-08-23	2003-03-27	Merckle Gmbh	Verfahren zur Herstellung von 6-(4-Chlorphenyl)-2,2-dimethyl-7-phnyl-2,3-dihydro-1H-pyrrolizin-5-yl-essigsäure
EP1427410A1 (en)	2001-08-30	2004-06-16	Merckle Gmbh	Use of annellated pyrrole compounds in the treatment of articular cartilage or subchondral bone degeneration
US6953787B2 (en)	2002-04-12	2005-10-11	Arena Pharmaceuticals, Inc.	5HT2C receptor modulators
MXPA05013364A (es)	2003-06-17	2006-03-17	Arena Pharm Inc	Procedimiento para preparar 3-benzazepinas.
US7704993B2 (en) *	2003-06-17	2010-04-27	Arena Pharmaceuticals, Inc.	Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
US20080009478A1 (en) *	2003-10-22	2008-01-10	Arena Pharmaceuticals, Inc.	Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases
US20070275949A1 (en) *	2003-10-22	2007-11-29	Arena Pharmaceuticals, Inc.	Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases
BRPI0519726B8 (pt)	2004-12-21	2021-05-25	Arena Pharm Inc	composto de hemidrato de (r)-8-cloro-1-metil-2,3,4,5-tetraidro-1h-3-benzazepina, composição compreendendo o referido composto e seus usos
BRPI0515862A2 (pt) *	2004-12-23	2011-10-11	Arena Pharm Inc	uso de fentermina e agonista seletivo do receptor de 5ht-2c na preparação de composições, composições moduladoras do receptor de 5ht-2c e forma de dosagem unitária compreendendo as mesmas
DE102005012971A1 (de)	2005-03-21	2006-09-28	Merckle Gmbh	Polymorphe Form von 6-(4-Chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl-essigsäure
JP5199997B2 (ja)	2006-04-03	2013-05-15	アリーナファーマシューティカルズ，インコーポレイテッド	８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス
JP5404414B2 (ja) *	2006-12-05	2014-01-29	アリーナファーマシューティカルズ，インコーポレイテッド	（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンおよびその中間体を調製するための方法
US8822727B2 (en) *	2008-03-04	2014-09-02	Arena Pharmaceuticals, Inc.	Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
WO2010148207A2 (en)	2009-06-18	2010-12-23	Arena Pharmaceuticals, Inc.	Processes for the preparation of 5-ht2c receptor agonists
KR20130112848A (ko)	2010-06-02	2013-10-14	아레나 파마슈티칼스, 인크.	5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법
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KR20130138770A (ko)	2010-09-01	2013-12-19	아레나 파마슈티칼스, 인크.	광학적으로 활성 산을 갖는 로르카세린의 염
US8999970B2 (en)	2010-09-01	2015-04-07	Arena Pharmaceuticals, Inc.	Administration of an anti-obesity compound to individuals with renal impairment
EP3485878A1 (en)	2010-09-01	2019-05-22	Arena Pharmaceuticals, Inc.	Modified-release dosage forms of 5-ht2c agonists useful for weight management
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1994
- 1994-06-01 DE DE4419315A patent/DE4419315A1/de not_active Withdrawn
1995
- 1995-05-31 JP JP50033396A patent/JP3569823B2/ja not_active Expired - Fee Related
- 1995-05-31 WO PCT/EP1995/002078 patent/WO1995032971A1/de not_active Ceased
- 1995-05-31 DK DK95921800T patent/DK0804437T3/da active
- 1995-05-31 US US08/737,920 patent/US5939415A/en not_active Expired - Fee Related
- 1995-05-31 AU AU26729/95A patent/AU2672995A/en not_active Abandoned
- 1995-05-31 ES ES95921800T patent/ES2248798T3/es not_active Expired - Lifetime
- 1995-05-31 AT AT95921800T patent/ATE304543T1/de not_active IP Right Cessation
- 1995-05-31 EP EP95921800A patent/EP0804437B1/de not_active Expired - Lifetime
- 1995-05-31 KR KR1019960706837A patent/KR100378882B1/ko not_active Expired - Fee Related
- 1995-05-31 CA CA002191745A patent/CA2191745A1/en not_active Abandoned
- 1995-05-31 DE DE59511017T patent/DE59511017D1/de not_active Expired - Fee Related
1996
- 1996-11-29 NO NO19965094A patent/NO311222B1/no unknown
- 1996-11-29 FI FI964772A patent/FI113966B/fi active

Also Published As

Publication number	Publication date
NO965094L (no)	1996-12-11
ATE304543T1 (de)	2005-09-15
FI964772L (fi)	1997-01-27
DE4419315A1 (de)	1995-12-07
EP0804437B1 (de)	2005-09-14
KR100378882B1 (ko)	2003-08-02
WO1995032971A1 (de)	1995-12-07
JPH10506369A (ja)	1998-06-23
CA2191745A1 (en)	1995-12-07
FI113966B (fi)	2004-07-15
AU2672995A (en)	1995-12-21
US5939415A (en)	1999-08-17
EP0804437A1 (de)	1997-11-05
FI964772A0 (fi)	1996-11-29
DK0804437T3 (da)	2005-11-14
KR970703345A (ko)	1997-07-03
DE59511017D1 (de)	2005-10-20
NO965094D0 (no)	1996-11-29
JP3569823B2 (ja)	2004-09-29
ES2248798T3 (es)	2006-03-16

Publication	Publication Date	Title
US5939415A (en)	1999-08-17	A!-annellated pyrrole derivatives and their use in pharmacology
FI114099B (fi)	2004-08-13	Pyrrolitsiini- ja pyrrolo[2,1-b] tiatsolijohdannaiset ja niiden käyttö farmasiassa
CA2723207C (en)	2016-07-12	Aminodihydrothiazine derivatives as bace inhibitors for the treatment of alzheimer's disease
AU605363B2 (en)	1991-01-10	4H-1-benzopyran-4-one derivative or its salt, processes for producing the same and pharmaceutical composition comprising the same as active ingredient
CA2191747C (en)	2007-01-23	(a)-annelated pyrrole derivatives and pharmaceutical use thereof
WO2004096781A1 (en)	2004-11-11	Use of derivatives of 2, 4-dihydro-[1,2,4]triazole-3-thione as inhibitors o fteh enzyme myeloperoxidase (mpo)
US4783472A (en)	1988-11-08	1H,3H-pyrrol[1,2-c]thiazole derivatives and pharmaceutical compositions containing them
AU2004212435A1 (en)	2004-08-26	Process for preparing pyrrolotriazine kinase inhibitors
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FI79319C (fi)	1989-12-11	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara tricykliska oxindolkarboxamidderivat.
HU178354B (en)	1982-04-28	Process for preparing 5-substituted 1,2-dihydro-3h-pyrrolo/1,2-a/-pyrrol-1-carboxylic acid derivatives from the corresponding nitriles
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IE913005A1 (en)	1992-03-11	Indolonaphthyridines
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US6743913B2 (en)	2004-06-01	Pyrrolothiazine and pyrrolothiazepine compounds having serotonin-2 receptor antagonistic and α-1-blocking action
MXPA04010765A (es)	2005-07-05	Procedimiento para la preparacion de clopidogrel.
JP3878128B2 (ja)	2007-02-07	チエノピロリジノン
Prešeren et al.	1999	Oxidative ring‐opening of rel‐(2R, 3R, 5S)‐5‐aryl‐2‐benzoylamino‐6, 7‐bis (methoxycarbonyl)‐2, 3‐dihydro‐1‐oxo‐3‐phenyl‐1H, 5H‐pyrazolo [1, 2‐a]‐pyrazoles. Synthesis of rel‐(2R, 3R)‐3‐phenyl‐3‐[5‐aryl‐3, 4‐bis (methoxycarbonyl) pyrazolyl‐1] alanine esters
CA2396413A1 (en)	2001-07-19	Fused pyrrole compounds, pharmaceutical agents containing the same, and the use thereof
NO792828L (no)	1980-03-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotienotiazin-derivater
US4927970A (en)	1990-05-22	Substituted 3-cyclobutene-1,2-dione intermediates
NO883219L (no)	1989-02-08	Framgangsmaate for framstilling av beta-lactam-forbindelse,mellomprodukt for framstilling av denne, og medisinske sammensetninger for behandling av bakteriologiske infeksjonssykdommer inneholdende denne.
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