CA1276158C - 4h-benzo[4,5]cyclohepta[1,2-b]thiophene derivatives - Google Patents
4h-benzo[4,5]cyclohepta[1,2-b]thiophene derivativesInfo
- Publication number
- CA1276158C CA1276158C CA000524731A CA524731A CA1276158C CA 1276158 C CA1276158 C CA 1276158C CA 000524731 A CA000524731 A CA 000524731A CA 524731 A CA524731 A CA 524731A CA 1276158 C CA1276158 C CA 1276158C
- Authority
- CA
- Canada
- Prior art keywords
- ester
- salt
- benzo
- compound
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 150000002148 esters Chemical class 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 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 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- LCBJLPHGCFFZHS-UHFFFAOYSA-N 2-(2-bromo-4-methoxybenzo[1,2]cyclohepta[3,4-b]thiophen-10-ylidene)acetic acid Chemical compound COC1=CC2=CC=CC=C2C(=CC(O)=O)C2=C1SC(Br)=C2 LCBJLPHGCFFZHS-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 9
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 8
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- 239000002221 antipyretic Substances 0.000 abstract description 5
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- -1 aliphatic alcohols Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010003246 arthritis Diseases 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 206010037660 Pyrexia Diseases 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229930194542 Keto Natural products 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 150000002085 enols Chemical group 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000001760 anti-analgesic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 235000010487 tragacanth Nutrition 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 1
- VKTNMDBSSPANFV-UHFFFAOYSA-N 2-bromo-4-methoxybenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound COC1=CC2=CC=CC=C2C(=O)C2=C1SC(Br)=C2 VKTNMDBSSPANFV-UHFFFAOYSA-N 0.000 description 1
- PVJOMVVOCZOHKX-UHFFFAOYSA-N 2-chloro-4-methoxybenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound COC1=CC2=CC=CC=C2C(=O)C2=C1SC(Cl)=C2 PVJOMVVOCZOHKX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000003500 enol ether group Chemical group 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000003108 foot joint Anatomy 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8530245 | 1985-12-09 | ||
| GB858530245A GB8530245D0 (en) | 1985-12-09 | 1985-12-09 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1276158C true CA1276158C (en) | 1990-11-13 |
Family
ID=10589437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524731A Expired - Lifetime CA1276158C (en) | 1985-12-09 | 1986-12-08 | 4h-benzo[4,5]cyclohepta[1,2-b]thiophene derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4775691A (en, 2012) |
| JP (1) | JPS62149672A (en, 2012) |
| AT (1) | ATA323986A (en, 2012) |
| AU (1) | AU600243B2 (en, 2012) |
| BE (1) | BE905872A (en, 2012) |
| CA (1) | CA1276158C (en, 2012) |
| CH (1) | CH672129B (en, 2012) |
| DE (1) | DE3641907A1 (en, 2012) |
| DK (1) | DK589886A (en, 2012) |
| ES (1) | ES2003176A6 (en, 2012) |
| FI (1) | FI864978A7 (en, 2012) |
| FR (1) | FR2595359B1 (en, 2012) |
| GB (2) | GB8530245D0 (en, 2012) |
| GR (1) | GR862863B (en, 2012) |
| HU (1) | HU202858B (en, 2012) |
| IL (1) | IL80906A (en, 2012) |
| IT (1) | IT1214756B (en, 2012) |
| LU (1) | LU86706A1 (en, 2012) |
| NL (1) | NL8603098A (en, 2012) |
| NZ (1) | NZ218547A (en, 2012) |
| PH (1) | PH24024A (en, 2012) |
| SE (1) | SE8605255L (en, 2012) |
| ZA (1) | ZA869296B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU203198B (en) * | 1987-10-26 | 1991-06-28 | Sandoz Ag | Process for producing pharmaceutical compositions having immunity-inhibiting, monokin-, particularly interleukin-1-inhibiting effect |
| GB9010332D0 (en) * | 1990-05-09 | 1990-06-27 | Sandoz Ltd | Improvements in or relating to organic compounds |
| AU2003256650A1 (en) * | 2002-07-19 | 2004-02-09 | Pharmacia Corporation | Substituted thiophene carboxamide compounds for the treatment of inflammation |
| WO2005096709A2 (en) * | 2004-03-11 | 2005-10-20 | Sun Pharmaceutical Industries Limited | A process for the preparation of 10,11-dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH473823A (de) * | 1964-08-11 | 1969-06-15 | Sandoz Ag | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
| US4137323A (en) * | 1973-10-10 | 1979-01-30 | Sandoz Ltd. | Organic compounds |
| DE2803984A1 (de) * | 1977-02-08 | 1978-08-10 | Sandoz Ag | Oxaminsaeurederivate, ihre herstellung und verwendung |
| US4496580A (en) * | 1981-07-23 | 1985-01-29 | Hoechst-Roussel Pharmaceuticals Inc. | Oxothienobenzoxepins |
| US4487778A (en) * | 1983-01-27 | 1984-12-11 | Fmc Corporation | Insecticidal esters derived from benzocycloalkane-thiophenemethyl compounds |
| HU195800B (en) * | 1983-10-13 | 1988-07-28 | Sandoz Ltd | Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them |
-
1985
- 1985-12-09 GB GB858530245A patent/GB8530245D0/en active Pending
-
1986
- 1986-12-03 CH CH482386A patent/CH672129B/de not_active IP Right Cessation
- 1986-12-05 ES ES8603303A patent/ES2003176A6/es not_active Expired
- 1986-12-05 GB GB8629130A patent/GB2183648B/en not_active Expired
- 1986-12-05 NL NL8603098A patent/NL8603098A/nl not_active Application Discontinuation
- 1986-12-05 AT AT0323986A patent/ATA323986A/de not_active Application Discontinuation
- 1986-12-08 DE DE19863641907 patent/DE3641907A1/de not_active Withdrawn
- 1986-12-08 NZ NZ218547A patent/NZ218547A/xx unknown
- 1986-12-08 SE SE8605255A patent/SE8605255L/xx not_active Application Discontinuation
- 1986-12-08 DK DK589886A patent/DK589886A/da not_active Application Discontinuation
- 1986-12-08 FR FR8617118A patent/FR2595359B1/fr not_active Expired
- 1986-12-08 FI FI864978A patent/FI864978A7/fi not_active IP Right Cessation
- 1986-12-08 LU LU86706A patent/LU86706A1/fr unknown
- 1986-12-08 IL IL80906A patent/IL80906A/xx not_active IP Right Cessation
- 1986-12-08 BE BE905872A patent/BE905872A/fr unknown
- 1986-12-08 JP JP61292269A patent/JPS62149672A/ja active Granted
- 1986-12-08 PH PH34565A patent/PH24024A/en unknown
- 1986-12-08 GR GR862863A patent/GR862863B/el unknown
- 1986-12-08 CA CA000524731A patent/CA1276158C/en not_active Expired - Lifetime
- 1986-12-08 AU AU66175/86A patent/AU600243B2/en not_active Ceased
- 1986-12-09 ZA ZA869296A patent/ZA869296B/xx unknown
- 1986-12-09 IT IT8648725A patent/IT1214756B/it active
-
1987
- 1987-01-15 HU HU87113A patent/HU202858B/hu unknown
-
1988
- 1988-01-20 US US07/145,870 patent/US4775691A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SE8605255L (sv) | 1987-06-10 |
| HU202858B (en) | 1991-04-29 |
| HUT46903A (en) | 1988-12-28 |
| PH24024A (en) | 1990-02-09 |
| JPH0422912B2 (en, 2012) | 1992-04-20 |
| GB2183648A (en) | 1987-06-10 |
| DK589886D0 (da) | 1986-12-08 |
| IL80906A0 (en) | 1987-03-31 |
| LU86706A1 (fr) | 1987-07-24 |
| FI864978A7 (fi) | 1987-06-10 |
| US4775691A (en) | 1988-10-04 |
| FI864978A0 (fi) | 1986-12-08 |
| IT8648725A0 (it) | 1986-12-09 |
| GB8629130D0 (en) | 1987-01-14 |
| AU600243B2 (en) | 1990-08-09 |
| IT1214756B (it) | 1990-01-18 |
| IL80906A (en) | 1991-01-31 |
| GR862863B (en) | 1987-04-09 |
| ATA323986A (de) | 1992-09-15 |
| ES2003176A6 (es) | 1988-10-16 |
| CH672129B (en, 2012) | 1989-10-31 |
| FR2595359B1 (fr) | 1989-08-18 |
| DE3641907A1 (de) | 1987-06-11 |
| GB8530245D0 (en) | 1986-01-22 |
| ZA869296B (en) | 1988-07-27 |
| FR2595359A1 (fr) | 1987-09-11 |
| SE8605255D0 (sv) | 1986-12-08 |
| NZ218547A (en) | 1990-03-27 |
| BE905872A (fr) | 1987-06-09 |
| AU6617586A (en) | 1987-06-11 |
| JPS62149672A (ja) | 1987-07-03 |
| NL8603098A (nl) | 1987-07-01 |
| DK589886A (da) | 1987-06-10 |
| GB2183648B (en) | 1989-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |