DD283815A5 - Verfahren zur herstellung von aromatischen und heterocyclischen carboxamiden - Google Patents
Verfahren zur herstellung von aromatischen und heterocyclischen carboxamiden Download PDFInfo
- Publication number
- DD283815A5 DD283815A5 DD89328832A DD32883289A DD283815A5 DD 283815 A5 DD283815 A5 DD 283815A5 DD 89328832 A DD89328832 A DD 89328832A DD 32883289 A DD32883289 A DD 32883289A DD 283815 A5 DD283815 A5 DD 283815A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydrogen
- alkyl
- reaction
- acid
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 230000008569 process Effects 0.000 title claims abstract description 5
- 150000003857 carboxamides Chemical class 0.000 title 1
- -1 heterocyclic carboxamides Chemical class 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 50
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- FYMYQYLZCXHPCY-UHFFFAOYSA-N 4-(3-piperidin-1-yl-3-pyrrolidin-1-ylthiomorpholin-4-yl)morpholine Chemical compound N1(CCCC1)C1(N(CCSC1)N1CCOCC1)N1CCCCC1 FYMYQYLZCXHPCY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 3
- JNEITSLVHAFZJK-UHFFFAOYSA-N 4-(diaminomethylideneamino)-n-(6-nitro-1,3-benzothiazol-2-yl)benzamide;hydrochloride Chemical compound Cl.C1=CC(NC(=N)N)=CC=C1C(=O)NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 JNEITSLVHAFZJK-UHFFFAOYSA-N 0.000 description 3
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
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- GHKHTBMTSUEBJD-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazol-2-amine Chemical compound ClC1=C(Cl)C=C2SC(N)=NC2=C1 GHKHTBMTSUEBJD-UHFFFAOYSA-N 0.000 description 2
- HMVMFLKTRSFJJF-UHFFFAOYSA-N 5-fluoro-1,3-benzothiazol-2-amine;hydrochloride Chemical compound Cl.FC1=CC=C2SC(N)=NC2=C1 HMVMFLKTRSFJJF-UHFFFAOYSA-N 0.000 description 2
- GIOCFNWQTZDWNE-UHFFFAOYSA-N 6-phenyl-1,3-benzothiazol-2-amine Chemical compound C1=C2SC(N)=NC2=CC=C1C1=CC=CC=C1 GIOCFNWQTZDWNE-UHFFFAOYSA-N 0.000 description 2
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- 229910017489 Cu I Inorganic materials 0.000 description 2
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 2
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- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BVUOEDOMUOJKOY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)ON1C(=O)CCC1=O BVUOEDOMUOJKOY-UHFFFAOYSA-N 0.000 description 1
- YETFLAUJROGBMC-UHFFFAOYSA-N (4-carboxyphenyl)-(diaminomethylidene)azanium;chloride Chemical compound Cl.NC(N)=NC1=CC=C(C(O)=O)C=C1 YETFLAUJROGBMC-UHFFFAOYSA-N 0.000 description 1
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
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- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
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- 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)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19803488A | 1988-05-24 | 1988-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283815A5 true DD283815A5 (de) | 1990-10-24 |
Family
ID=22731735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89328832A DD283815A5 (de) | 1988-05-24 | 1989-05-23 | Verfahren zur herstellung von aromatischen und heterocyclischen carboxamiden |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0343893B1 (cs) |
| JP (1) | JPH0678331B2 (cs) |
| KR (1) | KR910006864B1 (cs) |
| CN (1) | CN1023700C (cs) |
| AT (1) | ATE79114T1 (cs) |
| AU (1) | AU601905B2 (cs) |
| CA (1) | CA1328871C (cs) |
| DD (1) | DD283815A5 (cs) |
| DE (1) | DE68902358T2 (cs) |
| DK (1) | DK249389A (cs) |
| ES (1) | ES2043012T3 (cs) |
| FI (1) | FI892498A7 (cs) |
| GR (1) | GR3005844T3 (cs) |
| HU (1) | HU202507B (cs) |
| IE (1) | IE891667L (cs) |
| IL (1) | IL90337A0 (cs) |
| MX (1) | MX173140B (cs) |
| MY (1) | MY106035A (cs) |
| NO (1) | NO172389C (cs) |
| NZ (1) | NZ229234A (cs) |
| PL (1) | PL154875B1 (cs) |
| PT (1) | PT90622B (cs) |
| SU (1) | SU1681728A3 (cs) |
| YU (1) | YU47019B (cs) |
| ZA (1) | ZA893862B (cs) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2790299B2 (ja) * | 1989-02-01 | 1998-08-27 | 保土谷化学工業株式会社 | ペンゾチアゾール誘導体 |
| US5262400A (en) * | 1991-06-20 | 1993-11-16 | Merck & Co., Inc. | 4α-substituted avermectin derivatives |
| ES2161373T3 (es) | 1995-08-30 | 2001-12-01 | Searle & Co | Derivados de meta-guanidina, urea, tiourea o acido azaciclico-aminobenzoico como antagonistas de integrinas. |
| US6100423A (en) * | 1995-08-30 | 2000-08-08 | G. D. Searle & Co. | Amino benzenepropanoic acid compounds and derivatives thereof |
| US5716281A (en) * | 1995-11-27 | 1998-02-10 | Sega Enterprises, Ltd. | Game apparatus using a vehicle with an optical image synthesizing system |
| TW513418B (en) * | 1996-07-31 | 2002-12-11 | Otsuka Pharma Co Ltd | Thiazole derivatives, their production and use |
| CN1290165A (zh) | 1997-11-10 | 2001-04-04 | 布里斯托尔-迈尔斯斯奎布公司 | 苯并噻唑蛋白酪氨酸激酶抑制剂 |
| EP0928793B1 (en) * | 1998-01-02 | 2002-05-15 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| WO1999052861A1 (de) * | 1998-04-09 | 1999-10-21 | Institut für Diagnostikforschung GmbH an der Freien Universität Berlin | Neue benzylguanidinderivate für die therapie, in-vivo- und in-vitro-diagnostik |
| HRP20020962A2 (en) | 2000-06-21 | 2005-02-28 | F. Hoffmann - La Roche Ag | Benzothiazole derivatives |
| US6620811B2 (en) * | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
| US6599901B1 (en) * | 2001-11-19 | 2003-07-29 | Hoffman-La Roche Inc. | Pyridone substituted benzothiazole derivatives |
| US6624163B2 (en) | 2001-11-29 | 2003-09-23 | Hoffman-La Roche Inc. | Benzothiazole derivatives |
| GB0130868D0 (en) | 2001-12-24 | 2002-02-06 | Univ Strathclyde | New compounds |
| CN100357283C (zh) * | 2002-04-02 | 2007-12-26 | 中国科学院上海药物研究所 | 一类甲硫氨酰氨肽酶抑制剂 |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| WO2004101558A1 (en) * | 2003-05-13 | 2004-11-25 | F. Hoffmann-La Roche Ag | 2-imidazo-benzothiazoles as adenosine receptor ligands |
| JP4444290B2 (ja) * | 2003-05-19 | 2010-03-31 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシン受容体リガンドとしてのベンゾチアゾール誘導体 |
| CA2525102A1 (en) * | 2003-05-21 | 2004-12-02 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives and use thereof in the treatment of diseases relates to the adenosine a2a receptor |
| EP1633355B1 (en) * | 2003-05-30 | 2008-05-28 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives and use thereof in the treatment of diseases related to the adenosine a2a receptor |
| NZ544970A (en) * | 2003-07-28 | 2009-02-28 | Janssen Pharmaceutica Nv | Benzimidazole, benzthiazole and benzoxazole derivatives and their use as LTA4H modulators |
| SI1753760T1 (sl) | 2004-05-24 | 2008-04-30 | Hoffmann La Roche | (4-metoksi-7-morfolin-4-il-benzotiazol-2-il)-amid4- hidroksi-4-metil-piperidin-1-karboksilne kisline |
| RU2382782C2 (ru) * | 2004-07-22 | 2010-02-27 | Ф. Хоффманн-Ля Рош Аг | Производные бензотиазола |
| BRPI0513510A (pt) * | 2004-07-22 | 2008-05-06 | Hoffmann La Roche | benzotiazóis substituìdos |
| ES2309814T3 (es) | 2004-11-05 | 2008-12-16 | F. Hoffmann-La Roche Ag | Proceso para la obtencion de derivados del acido isonicotinico. |
| BRPI0609719B8 (pt) | 2005-03-23 | 2021-05-25 | Hoffmann La Roche | derivados de acetilenil-pirazol-pirimidina como antagonistas de mgbur2 |
| WO2007039439A1 (en) | 2005-09-27 | 2007-04-12 | F.Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mglur2 antagonists |
| EP1994017A2 (en) * | 2006-03-15 | 2008-11-26 | 4Sc Ag | Novel heterocyclic nf-kb inhibitors |
| GB0619325D0 (en) | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| US20110178070A1 (en) * | 2008-06-24 | 2011-07-21 | Takeda Pharmaceutical Company Limited | PI3K/mTOR INHIBITORS |
| US9499790B2 (en) | 2010-08-26 | 2016-11-22 | Kyoto University | Method for promoting differentiation of pluripotent stem cells into cardiac muscle cells |
| AU2012315953A1 (en) * | 2011-09-30 | 2014-04-03 | Kineta, Inc. | Anti-viral compounds |
| WO2013111875A1 (ja) | 2012-01-27 | 2013-08-01 | 国立大学法人京都大学 | 多能性幹細胞の心筋分化誘導法 |
| JP6351567B2 (ja) | 2013-03-08 | 2018-07-04 | 国立大学法人京都大学 | Ｅｇｆ受容体阻害剤を含む多能性幹細胞の心筋分化促進剤 |
| JP6333830B2 (ja) * | 2013-09-13 | 2018-05-30 | 国立大学法人京都大学 | 多能性幹細胞の心筋分化を促進する化合物 |
| JP6651218B2 (ja) | 2014-05-30 | 2020-02-19 | 国立大学法人京都大学 | 低分子化合物を用いた多能性幹細胞の心筋分化誘導法 |
| CN109776486A (zh) * | 2019-02-26 | 2019-05-21 | 武汉松石科技股份有限公司 | 一种硫酸亚丙酯的制备方法 |
| CN110590735B (zh) * | 2019-09-30 | 2021-07-23 | 江苏国泰超威新材料有限公司 | 一种环状硫酸酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61225168A (ja) * | 1985-03-30 | 1986-10-06 | Nippon Tokushu Noyaku Seizo Kk | 新規ベンズアミド、その製法及び殺虫剤 |
| KR930005004B1 (ko) * | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
| GB8611606D0 (en) * | 1986-05-13 | 1986-06-18 | Fbc Ltd | Fungicides |
-
1989
- 1989-05-18 IL IL90337A patent/IL90337A0/xx unknown
- 1989-05-22 ES ES89305141T patent/ES2043012T3/es not_active Expired - Lifetime
- 1989-05-22 EP EP89305141A patent/EP0343893B1/en not_active Expired - Lifetime
- 1989-05-22 DE DE8989305141T patent/DE68902358T2/de not_active Expired - Lifetime
- 1989-05-22 AT AT89305141T patent/ATE79114T1/de not_active IP Right Cessation
- 1989-05-22 JP JP1128600A patent/JPH0678331B2/ja not_active Expired - Lifetime
- 1989-05-22 PT PT90622A patent/PT90622B/pt not_active IP Right Cessation
- 1989-05-23 DK DK249389A patent/DK249389A/da unknown
- 1989-05-23 HU HU892578A patent/HU202507B/hu not_active IP Right Cessation
- 1989-05-23 FI FI892498A patent/FI892498A7/fi not_active Application Discontinuation
- 1989-05-23 ZA ZA893862A patent/ZA893862B/xx unknown
- 1989-05-23 IE IE891667A patent/IE891667L/xx unknown
- 1989-05-23 DD DD89328832A patent/DD283815A5/de not_active IP Right Cessation
- 1989-05-23 CA CA000600370A patent/CA1328871C/en not_active Expired - Fee Related
- 1989-05-23 MY MYPI89000689A patent/MY106035A/en unknown
- 1989-05-23 AU AU35098/89A patent/AU601905B2/en not_active Ceased
- 1989-05-23 NZ NZ229234A patent/NZ229234A/en unknown
- 1989-05-23 MX MX016158A patent/MX173140B/es unknown
- 1989-05-23 SU SU894614242A patent/SU1681728A3/ru active
- 1989-05-23 KR KR1019890006889A patent/KR910006864B1/ko not_active Expired
- 1989-05-23 NO NO892059A patent/NO172389C/no unknown
- 1989-05-24 CN CN89103540A patent/CN1023700C/zh not_active Expired - Fee Related
- 1989-05-24 YU YU105989A patent/YU47019B/sh unknown
- 1989-05-24 PL PL1989279613A patent/PL154875B1/pl unknown
-
1992
- 1992-09-30 GR GR920402178T patent/GR3005844T3/el unknown
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| ENJ | Ceased due to non-payment of renewal fee |