NO880088L - 2,1-benzotiazepin-2,2-dioksyd-5-karboksylsyrederivater. - Google Patents

2,1-benzotiazepin-2,2-dioksyd-5-karboksylsyrederivater.

Info

Publication number: NO880088L
Authority: NO; Norway
Prior art keywords: alkyl; phenyl; stands; halogen; formula
Prior art date: 1987-01-12

Application number

NO880088A

Other languages

English (en)

Norwegian (no)

Other versions

NO880088D0 (no

Inventor

Jan W F Wasley

Original Assignee

Ciba Geigy Ag

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.)

1987-01-12

Filing date

1988-01-11

Publication date

1988-07-13

1988-01-11 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1988-01-11 Publication of NO880088D0 publication Critical patent/NO880088D0/no

1988-07-13 Publication of NO880088L publication Critical patent/NO880088L/no

Links

150000001875 compounds Chemical class 0.000 claims description 110
125000000217 alkyl group Chemical group 0.000 claims description 68
229910052736 halogen Inorganic materials 0.000 claims description 67
150000002367 halogens Chemical class 0.000 claims description 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
-1 heterocyclic aryl radical Chemical class 0.000 claims description 55
150000003839 salts Chemical class 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 46
238000000034 method Methods 0.000 claims description 44
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
150000002431 hydrogen Chemical class 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
125000003545 alkoxy group Chemical group 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 21
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
150000001721 carbon Chemical group 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 18
229910052740 iodine Inorganic materials 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
150000002170 ethers Chemical class 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229910052760 oxygen Chemical class 0.000 claims description 6
239000001301 oxygen Chemical class 0.000 claims description 6
239000011593 sulfur Chemical class 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
150000002081 enamines Chemical class 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000005956 isoquinolyl group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
125000002837 carbocyclic group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
VEKCSEJDLMVSSE-UHFFFAOYSA-N 3-benzyl-N-(4-chlorophenyl)-1-[(4-chlorophenyl)methyl]-4-hydroxy-2,2-dioxo-3H-2lambda6,1-benzothiazepine-5-carboxamide Chemical compound C12=CC=CC=C2N(CC=2C=CC(Cl)=CC=2)S(=O)(=O)C(CC=2C=CC=CC=2)C(O)=C1C(=O)NC1=CC=C(Cl)C=C1 VEKCSEJDLMVSSE-UHFFFAOYSA-N 0.000 claims description 2
ZBEIGTVYIHPXMK-UHFFFAOYSA-N COClSC Chemical compound COClSC ZBEIGTVYIHPXMK-UHFFFAOYSA-N 0.000 claims description 2
150000002466 imines Chemical class 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 33
239000000243 solution Substances 0.000 description 33
238000007710 freezing Methods 0.000 description 30
230000008014 freezing Effects 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
241000124008 Mammalia Species 0.000 description 16
239000002585 base Substances 0.000 description 16
239000007858 starting material Substances 0.000 description 15
210000000440 neutrophil Anatomy 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
239000002904 solvent Substances 0.000 description 13
230000005764 inhibitory process Effects 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
238000010992 reflux Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000015556 catabolic process Effects 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000005907 alkyl ester group Chemical group 0.000 description 8
210000000845 cartilage Anatomy 0.000 description 8
239000000825 pharmaceutical preparation Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
230000004913 activation Effects 0.000 description 7
239000013543 active substance Substances 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000004494 ethyl ester group Chemical group 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
102000055008 Matrilin Proteins Human genes 0.000 description 5
108010072582 Matrilin Proteins Proteins 0.000 description 5
241000700159 Rattus Species 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000003399 chemotactic effect Effects 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
201000008482 osteoarthritis Diseases 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 4
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
230000035876 healing Effects 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
239000012876 carrier material Substances 0.000 description 3
238000006243 chemical reaction Methods 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
238000001816 cooling Methods 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
BWQBYHGDMBHIIQ-UHFFFAOYSA-N methyl 2-(2-aminophenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1N BWQBYHGDMBHIIQ-UHFFFAOYSA-N 0.000 description 3
AEPIHYWYPKENIN-UHFFFAOYSA-N methyl 2-[2-[(4-chlorophenyl)methyl-(2-ethoxy-2-oxoethyl)sulfonylamino]phenyl]acetate Chemical compound C=1C=CC=C(CC(=O)OC)C=1N(S(=O)(=O)CC(=O)OCC)CC1=CC=C(Cl)C=C1 AEPIHYWYPKENIN-UHFFFAOYSA-N 0.000 description 3
VKCJZFHQDHTULO-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[(4-chlorophenyl)methyl]-4-hydroxy-2,2-dioxo-3h-2$l^{6},1-benzothiazepine-5-carboxamide Chemical compound C12=CC=CC=C2N(CC=2C=CC(Cl)=CC=2)S(=O)(=O)CC(O)=C1C(=O)NC1=CC=C(Cl)C=C1 VKCJZFHQDHTULO-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
201000003068 rheumatic fever Diseases 0.000 description 3
206010039073 rheumatoid arthritis Diseases 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 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
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
238000009825 accumulation Methods 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
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150000001299 aldehydes Chemical class 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000002917 arthritic effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000027455 binding Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
230000003846 cartilage breakdown Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications

- 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
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO880088A 1987-01-12 1988-01-11 2,1-benzotiazepin-2,2-dioksyd-5-karboksylsyrederivater. NO880088L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/002,074 US4803197A (en)	1987-01-12	1987-01-12	2,1-benzothiazepine-2,2-dioxide-5-carboxylic acid derivatives

Publications (2)

Publication Number	Publication Date
NO880088D0 NO880088D0 (no)	1988-01-11
NO880088L true NO880088L (no)	1988-07-13

Family

ID=21699148

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO880088A NO880088L (no)	1987-01-12	1988-01-11	2,1-benzotiazepin-2,2-dioksyd-5-karboksylsyrederivater.

Country Status (15)

Country	Link
US (1)	US4803197A (da)
EP (1)	EP0276194A1 (da)
JP (1)	JPS63174980A (da)
KR (1)	KR880009002A (da)
AU (1)	AU1016288A (da)
DD (1)	DD270909A5 (da)
DK (1)	DK9588A (da)
FI (1)	FI880081A7 (da)
HU (1)	HU198917B (da)
IL (1)	IL85037A0 (da)
NO (1)	NO880088L (da)
NZ (1)	NZ223138A (da)
PH (1)	PH23637A (da)
PT (1)	PT86519B (da)
ZA (1)	ZA88145B (da)

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ES2046941B1 (es) *	1991-10-24	1994-08-16	Consejo Superior Investigacion	Procedimiento de obtencion de trioxo-pirazolo, (2,1) benzotiazepinas>
ES2040629B1 (es) *	1991-12-18	1994-06-16	Consejo Superior Investigacion	Procedimiento de obtencion de derivados triciclicos de la benzotiazepina farmacologicamente activos.
UA59384C2 (uk)	1996-12-20	2003-09-15	Пфайзер, Інк.	Похідні сульфонамідів та амідів як агоністи простагландину, фармацевтична композиція та способи лікування на їх основі

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Publication number	Priority date	Publication date	Assignee	Title
US3962261A (en) *	1974-02-04	1976-06-08	Warner-Lambert Company	2,3,4,5-tetra hydro-5-oxo-1-benzothiepi n-4-carboxamide 1,1-dioxides
SE420725B (sv) *	1974-09-26	1981-10-26	Ciba Geigy Ag	Sett att framstella 2,3-dihydro-1-benstiepin-4-karboxylsyraamider
DE2756113A1 (de) *	1977-12-16	1979-06-21	Thomae Gmbh Dr K	Neue 4-hydroxy-2h-1,2-benzothiazin- 3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4582850A (en) *	1985-02-28	1986-04-15	Ciba-Geigy Corporation	Topical and systemic treatment of psoriasis using 7-chloro-N-(3,4-dichlorophenyl)-2,3-dihydro-5-hydroxy-1-benzothiepin-4-carboxamide 1,1-dioxide and pharmaceutically acceptable salts thereof
US4605665A (en) *	1985-02-28	1986-08-12	Ciba-Geigy Corporation	Systemic treatment of splanchnic ischemia shock using 7-chloro-N-(3,4-dichlorophenyl)-2,3-dihydro-5-hydroxy-1-benzothiepin-4-carboxamide 1,1-dioxide and pharmaceutically acceptable salts thereof

1987
- 1987-01-12 US US07/002,074 patent/US4803197A/en not_active Expired - Fee Related
1988
- 1988-01-06 EP EP88810004A patent/EP0276194A1/de not_active Withdrawn
- 1988-01-06 PH PH36325A patent/PH23637A/en unknown
- 1988-01-06 IL IL85037A patent/IL85037A0/xx unknown
- 1988-01-08 NZ NZ223138A patent/NZ223138A/xx unknown
- 1988-01-08 FI FI880081A patent/FI880081A7/fi not_active IP Right Cessation
- 1988-01-08 DD DD88312142A patent/DD270909A5/de unknown
- 1988-01-11 AU AU10162/88A patent/AU1016288A/en not_active Abandoned
- 1988-01-11 HU HU8891A patent/HU198917B/hu not_active IP Right Cessation
- 1988-01-11 PT PT86519A patent/PT86519B/pt not_active IP Right Cessation
- 1988-01-11 JP JP63002643A patent/JPS63174980A/ja active Pending
- 1988-01-11 DK DK009588A patent/DK9588A/da not_active Application Discontinuation
- 1988-01-11 ZA ZA880145A patent/ZA88145B/xx unknown
- 1988-01-11 NO NO880088A patent/NO880088L/no unknown
- 1988-01-12 KR KR1019880000148A patent/KR880009002A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
NZ223138A (en)	1990-02-26
KR880009002A (ko)	1988-09-13
IL85037A0 (en)	1988-06-30
ZA88145B (en)	1988-07-12
DK9588A (da)	1988-07-13
DD270909A5 (de)	1989-08-16
PH23637A (en)	1989-09-27
FI880081A0 (fi)	1988-01-08
US4803197A (en)	1989-02-07
NO880088D0 (no)	1988-01-11
PT86519A (en)	1988-02-01
JPS63174980A (ja)	1988-07-19
EP0276194A1 (de)	1988-07-27
FI880081A7 (fi)	1988-07-13
HUT47262A (en)	1989-02-28
AU1016288A (en)	1988-07-14
HU198917B (en)	1989-12-28
DK9588D0 (da)	1988-01-11
PT86519B (pt)	1991-12-31

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