NO800946L - Fremgangsmaate ved fremstilling av benzothiazolderivater - Google Patents
Fremgangsmaate ved fremstilling av benzothiazolderivaterInfo
- Publication number
- NO800946L NO800946L NO800946A NO800946A NO800946L NO 800946 L NO800946 L NO 800946L NO 800946 A NO800946 A NO 800946A NO 800946 A NO800946 A NO 800946A NO 800946 L NO800946 L NO 800946L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- formula
- solution
- phenyl
- salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- DPRKTNKWAXPYNW-UHFFFAOYSA-N 2-(2-phenyl-1,3-benzothiazol-6-yl)propanoic acid Chemical compound S1C2=CC(C(C(O)=O)C)=CC=C2N=C1C1=CC=CC=C1 DPRKTNKWAXPYNW-UHFFFAOYSA-N 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 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 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 229910001411 inorganic cation Inorganic materials 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- -1 alkali metal cations Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- NQLZMYCPUWKQCF-UHFFFAOYSA-N 2-(2-amino-1,3-benzothiazol-6-yl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C2N=C(N)SC2=C1 NQLZMYCPUWKQCF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 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
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- WOMVICAMAQURRN-UHFFFAOYSA-N 2-(4-aminophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(N)C=C1 WOMVICAMAQURRN-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000005365 aminothiol group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- LOFJQNDBIMICJE-UHFFFAOYSA-M sodium 2-(2-phenyl-1,3-benzothiazol-6-yl)propanoate Chemical compound C1(=CC=CC=C1)C=1SC2=C(N1)C=CC(=C2)C(C(=O)[O-])C.[Na+] LOFJQNDBIMICJE-UHFFFAOYSA-M 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7908303A FR2453163A1 (fr) | 1979-04-03 | 1979-04-03 | Derives de benzothiazole, leur procede de preparation et leurs applications en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO800946L true NO800946L (no) | 1980-10-06 |
Family
ID=9223868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO800946A NO800946L (no) | 1979-04-03 | 1980-04-01 | Fremgangsmaate ved fremstilling av benzothiazolderivater |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0017543B1 (es) |
| JP (1) | JPS55133367A (es) |
| AR (1) | AR227884A1 (es) |
| AT (1) | ATE4807T1 (es) |
| AU (1) | AU530911B2 (es) |
| BE (1) | BE882270A (es) |
| CA (1) | CA1144556A (es) |
| DD (1) | DD151448A5 (es) |
| DE (1) | DE3065004D1 (es) |
| DK (1) | DK134880A (es) |
| ES (2) | ES8200098A1 (es) |
| FI (1) | FI801023A (es) |
| FR (1) | FR2453163A1 (es) |
| GR (1) | GR67195B (es) |
| HU (1) | HU178851B (es) |
| IL (1) | IL59655A (es) |
| IT (1) | IT8048308A0 (es) |
| MA (1) | MA18772A1 (es) |
| NO (1) | NO800946L (es) |
| NZ (1) | NZ193337A (es) |
| OA (1) | OA06504A (es) |
| PH (1) | PH15451A (es) |
| PL (1) | PL123701B1 (es) |
| PT (1) | PT71035A (es) |
| SU (1) | SU910120A3 (es) |
| YU (1) | YU80780A (es) |
| ZA (1) | ZA801574B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003203227A1 (en) | 2002-02-05 | 2003-09-02 | Sumitomo Chemical Company, Limited | Process for producing biaryl compound |
| BR112013000043A2 (pt) | 2010-07-02 | 2019-09-24 | Gilead Sciences Inc | derivados de ácido naft-2-ilacético para tratar aids |
| NZ604716A (en) | 2010-07-02 | 2014-12-24 | Gilead Sciences Inc | 2-quinolinyl-acetic acid derivatives as hiv antiviral compounds |
| SG194512A1 (en) * | 2011-04-21 | 2013-12-30 | Gilead Sciences Inc | Benzothiazole compounds and their pharmaceutical use |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| WO2013103724A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | 2- (tert - butoxy) -2- (7 -methylquinolin- 6 - yl) acetic acid derivatives for treating aids |
| ES2571479T3 (es) | 2012-04-20 | 2016-05-25 | Gilead Sciences Inc | Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2145178C3 (de) * | 1970-09-11 | 1975-12-11 | Tokyo Tanabe Co., Ltd., Tokio | 2-Phenyl-5-oder -6-benzothiazolylessigsäure-Verblndungen |
| US3895028A (en) * | 1972-09-12 | 1975-07-15 | Tokyo Tanabe Co | Alpha-(2-phenylbenzothiazol-5-yl)propionic acid |
-
1979
- 1979-04-03 FR FR7908303A patent/FR2453163A1/fr active Granted
-
1980
- 1980-03-10 MA MA18970A patent/MA18772A1/fr unknown
- 1980-03-17 BE BE0/199830A patent/BE882270A/fr not_active IP Right Cessation
- 1980-03-17 GR GR61462A patent/GR67195B/el unknown
- 1980-03-18 IL IL59655A patent/IL59655A/xx unknown
- 1980-03-18 ZA ZA00801574A patent/ZA801574B/xx unknown
- 1980-03-19 AT AT80400368T patent/ATE4807T1/de not_active IP Right Cessation
- 1980-03-19 DE DE8080400368T patent/DE3065004D1/de not_active Expired
- 1980-03-19 EP EP80400368A patent/EP0017543B1/fr not_active Expired
- 1980-03-24 YU YU00807/80A patent/YU80780A/xx unknown
- 1980-03-26 AU AU56864/80A patent/AU530911B2/en not_active Ceased
- 1980-03-28 PT PT71035A patent/PT71035A/pt unknown
- 1980-03-28 DK DK134880A patent/DK134880A/da not_active Application Discontinuation
- 1980-03-31 AR AR280502A patent/AR227884A1/es active
- 1980-04-01 NO NO800946A patent/NO800946L/no unknown
- 1980-04-01 PH PH23847A patent/PH15451A/en unknown
- 1980-04-01 IT IT8048308A patent/IT8048308A0/it unknown
- 1980-04-01 CA CA000348939A patent/CA1144556A/en not_active Expired
- 1980-04-01 FI FI801023A patent/FI801023A/fi not_active Application Discontinuation
- 1980-04-01 SU SU802901454A patent/SU910120A3/ru active
- 1980-04-01 ES ES490797A patent/ES8200098A1/es not_active Expired
- 1980-04-02 PL PL1980223191A patent/PL123701B1/pl unknown
- 1980-04-02 DD DD80220177A patent/DD151448A5/de unknown
- 1980-04-02 HU HU8080789A patent/HU178851B/hu unknown
- 1980-04-02 NZ NZ193337A patent/NZ193337A/xx unknown
- 1980-04-03 JP JP4402480A patent/JPS55133367A/ja active Pending
- 1980-04-03 OA OA57074A patent/OA06504A/xx unknown
- 1980-12-11 ES ES498313A patent/ES8204989A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU80780A (en) | 1983-02-28 |
| AR227884A1 (es) | 1982-12-30 |
| IL59655A (en) | 1983-05-15 |
| IT8048308A0 (it) | 1980-04-01 |
| JPS55133367A (en) | 1980-10-17 |
| CA1144556A (en) | 1983-04-12 |
| NZ193337A (en) | 1982-12-07 |
| PL123701B1 (en) | 1982-11-30 |
| FR2453163A1 (fr) | 1980-10-31 |
| FI801023A (fi) | 1980-10-04 |
| ES490797A0 (es) | 1981-11-01 |
| DK134880A (da) | 1980-10-04 |
| OA06504A (fr) | 1981-07-31 |
| BE882270A (fr) | 1980-09-17 |
| ATE4807T1 (de) | 1983-10-15 |
| ES8200098A1 (es) | 1981-11-01 |
| DD151448A5 (de) | 1981-10-21 |
| PH15451A (en) | 1983-01-18 |
| PL223191A1 (es) | 1981-01-30 |
| GR67195B (es) | 1981-06-24 |
| EP0017543B1 (fr) | 1983-09-28 |
| FR2453163B1 (es) | 1982-07-02 |
| SU910120A3 (ru) | 1982-02-28 |
| DE3065004D1 (en) | 1983-11-03 |
| IL59655A0 (en) | 1980-06-30 |
| MA18772A1 (fr) | 1980-10-01 |
| ES498313A0 (es) | 1982-06-01 |
| AU5686480A (en) | 1980-10-09 |
| PT71035A (fr) | 1980-04-01 |
| ES8204989A1 (es) | 1982-06-01 |
| AU530911B2 (en) | 1983-08-04 |
| ZA801574B (en) | 1981-03-25 |
| HU178851B (en) | 1982-07-28 |
| EP0017543A1 (fr) | 1980-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5719168A (en) | Acetamide derivatives and their use as feeding behaviour modifiers | |
| US3641127A (en) | (3-benzoylphenyl) alkanoic acids | |
| US6180793B1 (en) | Process for the preparation of a pharmacologically active substance | |
| US6258961B1 (en) | Intermediates and process for the preparation thereof | |
| DK158346B (da) | Analogifremgangsmaade til fremstilling af 4-amino-5-alkylsulfonyl-o-anisamid-derivater samt 2-methoxy-4-amino-5-alkylsulfonylbenzoesyrer til anvendelse som mellemprodukter ved fremgangsmaaden | |
| CS198222B2 (en) | Method of producing derivatives of quinazolone | |
| NO760993L (es) | ||
| US4064247A (en) | Thiazolo[3,4-b]isoquinoline derivatives and pharmaceutical compositions containing them | |
| NO800946L (no) | Fremgangsmaate ved fremstilling av benzothiazolderivater | |
| US2638472A (en) | 1-benzyl-5, 6, 7, 8-tetrahydroisoquinoline and derivatives thereof | |
| DK149230B (da) | Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf | |
| US2728779A (en) | Esters of substituted aminobutanes | |
| US4659728A (en) | Hydroxy substituted 4,5-diphenyl-2-oxazole propanoic acid | |
| DE69836331T2 (de) | 2-sulfamoylbenzoesäure-derivate | |
| CS216205B2 (en) | Method of making the derivatives of the 1,4-diphenylpyrazole | |
| US4906757A (en) | Process for the preparation of dextrorotatory 3-(3-pyridyl)-1H,3H-pyrrolo [1,2-c]-7-thiazolecarboxylic acid | |
| EP0012801A1 (de) | 2-(1-Phenyl-2,5-cyclohexadienyl)-äthylaminderivate, Verfahren zu deren Herstellung, deren Verwendung als pharmazeutische Wirkstoffe sowie diese enthaltende Arzneimittel | |
| JPS6360015B2 (es) | ||
| JPS6019317B2 (ja) | チエノチアジン誘導体及びその製造方法 | |
| US3894057A (en) | Tetrahydrobenzofuranylphenoxycarboxylic acids, esters | |
| US4189607A (en) | Anilionotropone derivatives | |
| DK172604B1 (da) | Benzocykloheptenderivater samt farmaceutiske midler indeholde disse | |
| US3946019A (en) | 7H-Indolizino [5,6,7-IJ]isoquinoline derivatives | |
| DE69002983T2 (de) | Thioformamid-Derivate. | |
| EP0153678A1 (en) | Cinnamic acid derivatives, processes for the preparation thereof and pharmaceutical compositions |