CN1023700C - 芳族及杂环甲酰胺衍生物抗肿瘤剂的制备 - Google Patents
芳族及杂环甲酰胺衍生物抗肿瘤剂的制备 Download PDFInfo
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- CN1023700C CN1023700C CN89103540A CN89103540A CN1023700C CN 1023700 C CN1023700 C CN 1023700C CN 89103540 A CN89103540 A CN 89103540A CN 89103540 A CN89103540 A CN 89103540A CN 1023700 C CN1023700 C CN 1023700C
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- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- -1 Heterocyclic Formamide Derivatives Chemical class 0.000 title claims description 24
- 239000002246 antineoplastic agent Substances 0.000 title abstract description 10
- 125000003118 aryl group Chemical group 0.000 title 1
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 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
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical group OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims description 2
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- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
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- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical class [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 150000002431 hydrogen Chemical class 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
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- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 238000003756 stirring Methods 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-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
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 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 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
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- 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 4
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- 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 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 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
- 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 3
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- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 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
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- LNJDLEPJBKSURC-UHFFFAOYSA-N tert-butyl n-[2-[[4-[(5-fluoro-1,3-benzothiazol-2-yl)carbamoyl]-1,3-thiazol-2-yl]sulfanyl]ethyl]carbamate Chemical compound S1C(SCCNC(=O)OC(C)(C)C)=NC(C(=O)NC=2SC3=CC=C(F)C=C3N=2)=C1 LNJDLEPJBKSURC-UHFFFAOYSA-N 0.000 description 1
- AONALDXKEVVTDC-UHFFFAOYSA-N tert-butyl n-[2-[[4-[(5-fluoro-3-methyl-2h-1,3-benzothiazol-2-yl)carbamoyl]-1,3-thiazol-2-yl]sulfanyl]ethyl]carbamate Chemical compound S1C2=CC=C(F)C=C2N(C)C1NC(=O)C1=CSC(SCCNC(=O)OC(C)(C)C)=N1 AONALDXKEVVTDC-UHFFFAOYSA-N 0.000 description 1
- BOZNUSZXGHDEJM-UHFFFAOYSA-N tert-butyl n-[2-[[4-[(6-phenyl-1,3-benzothiazol-2-yl)carbamoyl]-1,3-thiazol-2-yl]sulfanyl]ethyl]carbamate Chemical compound S1C(SCCNC(=O)OC(C)(C)C)=NC(C(=O)NC=2SC3=CC(=CC=C3N=2)C=2C=CC=CC=2)=C1 BOZNUSZXGHDEJM-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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
-
- 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
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)
- 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19803488A | 1988-05-24 | 1988-05-24 | |
| US198,034 | 1988-05-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1037898A CN1037898A (zh) | 1989-12-13 |
| CN1023700C true CN1023700C (zh) | 1994-02-09 |
Family
ID=22731735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89103540A Expired - Fee Related CN1023700C (zh) | 1988-05-24 | 1989-05-24 | 芳族及杂环甲酰胺衍生物抗肿瘤剂的制备 |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0343893B1 (enExample) |
| JP (1) | JPH0678331B2 (enExample) |
| KR (1) | KR910006864B1 (enExample) |
| CN (1) | CN1023700C (enExample) |
| AT (1) | ATE79114T1 (enExample) |
| AU (1) | AU601905B2 (enExample) |
| CA (1) | CA1328871C (enExample) |
| DD (1) | DD283815A5 (enExample) |
| DE (1) | DE68902358T2 (enExample) |
| DK (1) | DK249389A (enExample) |
| ES (1) | ES2043012T3 (enExample) |
| FI (1) | FI892498A7 (enExample) |
| GR (1) | GR3005844T3 (enExample) |
| HU (1) | HU202507B (enExample) |
| IE (1) | IE891667L (enExample) |
| IL (1) | IL90337A0 (enExample) |
| MX (1) | MX173140B (enExample) |
| MY (1) | MY106035A (enExample) |
| NO (1) | NO172389C (enExample) |
| NZ (1) | NZ229234A (enExample) |
| PL (1) | PL154875B1 (enExample) |
| PT (1) | PT90622B (enExample) |
| SU (1) | SU1681728A3 (enExample) |
| YU (1) | YU47019B (enExample) |
| ZA (1) | ZA893862B (enExample) |
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 |
| PL186370B1 (pl) * | 1995-08-30 | 2003-12-31 | Searle & Co | Związki, pochodne kwasu aminobenzoesowego, zawierające je kompozycje farmaceutyczne oraz zastosowanie tych związków |
| 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 |
| NZ503491A (en) | 1997-11-10 | 2002-08-28 | Bristol Myers Squibb Co | 2-substituted amino-1,3-benzothiazole derivatives useful as protein tyrosine kinase inhibitors |
| 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 |
| CN100372844C (zh) * | 2003-05-13 | 2008-03-05 | 弗·哈夫曼-拉罗切有限公司 | 作为腺苷受体配体的2-咪唑-苯并噻唑 |
| 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 |
| BRPI0410754A (pt) * | 2003-05-21 | 2006-06-27 | Hoffmann La Roche | derivados de benzotiazol e uso desses derivados no tratamento de doenças relacionadas com o receptor de adenosina a2a |
| AU2004243481B2 (en) * | 2003-05-30 | 2008-10-09 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives and use thereof in the treatment of diseases related to the adenosine A2A receptor |
| BRPI0413072A (pt) * | 2003-07-28 | 2006-10-03 | Janssen Pharmaceutica Nv | moduladores de lta4h |
| DE602005004142T2 (de) | 2004-05-24 | 2009-01-02 | F. Hoffmann-La Roche Ag | 4-hydroxy-4-methylpiperidin-1-carbonsäure-(4-methoxy-7-morpholin-4-ylbenzothiazol-2-yl)-amid |
| CA2574193C (en) * | 2004-07-22 | 2013-03-05 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives as adenosine receptor ligands |
| RU2381227C2 (ru) * | 2004-07-22 | 2010-02-10 | Ф. Хоффманн-Ля Рош Аг | Замещенные бензотиазолы |
| WO2006048172A1 (en) | 2004-11-05 | 2006-05-11 | F. Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| DK1863818T3 (da) | 2005-03-23 | 2010-05-10 | Hoffmann La Roche | Acetylenyl-pyrazolo-pyrimidinderivater som mglur2-antagonister |
| DE602006013493D1 (de) | 2005-09-27 | 2010-05-20 | Hoffmann La Roche | Oxadiazolylpyrazolopyrimidine als mglur2-antagonisten |
| CN101405278A (zh) * | 2006-03-15 | 2009-04-08 | 4Sc股份公司 | 新颖的杂环NF-κB抑制剂 |
| GB0619325D0 (en) | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| WO2010008847A2 (en) * | 2008-06-24 | 2010-01-21 | Takeda Pharmaceutical Company Limited | Pi3k/m tor inhibitors |
| US9499790B2 (en) | 2010-08-26 | 2016-11-22 | Kyoto University | Method for promoting differentiation of pluripotent stem cells into cardiac muscle cells |
| KR20140070631A (ko) * | 2011-09-30 | 2014-06-10 | 키네타, 인크. | 항바이러스 화합물 |
| KR101996343B1 (ko) | 2012-01-27 | 2019-07-05 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 전능성 줄기세포의 심근분화 유도방법 |
| US10196609B2 (en) | 2013-03-08 | 2019-02-05 | Kyoto University | Composition for promoting cardiac differentiation of pluripotent stem cell comprising EGFR inhibitor |
| WO2015037706A1 (ja) * | 2013-09-13 | 2015-03-19 | 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 DE DE8989305141T patent/DE68902358T2/de not_active Expired - Lifetime
- 1989-05-22 JP JP1128600A patent/JPH0678331B2/ja not_active Expired - Lifetime
- 1989-05-22 ES ES89305141T patent/ES2043012T3/es not_active Expired - Lifetime
- 1989-05-22 PT PT90622A patent/PT90622B/pt not_active IP Right Cessation
- 1989-05-22 AT AT89305141T patent/ATE79114T1/de not_active IP Right Cessation
- 1989-05-22 EP EP89305141A patent/EP0343893B1/en not_active Expired - Lifetime
- 1989-05-23 ZA ZA893862A patent/ZA893862B/xx unknown
- 1989-05-23 DD DD89328832A patent/DD283815A5/de not_active IP Right Cessation
- 1989-05-23 DK DK249389A patent/DK249389A/da unknown
- 1989-05-23 AU AU35098/89A patent/AU601905B2/en not_active Ceased
- 1989-05-23 KR KR1019890006889A patent/KR910006864B1/ko not_active Expired
- 1989-05-23 NZ NZ229234A patent/NZ229234A/en unknown
- 1989-05-23 HU HU892578A patent/HU202507B/hu not_active IP Right Cessation
- 1989-05-23 MY MYPI89000689A patent/MY106035A/en unknown
- 1989-05-23 CA CA000600370A patent/CA1328871C/en not_active Expired - Fee Related
- 1989-05-23 MX MX016158A patent/MX173140B/es unknown
- 1989-05-23 IE IE891667A patent/IE891667L/xx unknown
- 1989-05-23 SU SU894614242A patent/SU1681728A3/ru active
- 1989-05-23 FI FI892498A patent/FI892498A7/fi not_active Application Discontinuation
- 1989-05-23 NO NO892059A patent/NO172389C/no unknown
- 1989-05-24 PL PL1989279613A patent/PL154875B1/pl unknown
- 1989-05-24 YU YU105989A patent/YU47019B/sh unknown
- 1989-05-24 CN CN89103540A patent/CN1023700C/zh not_active Expired - Fee Related
-
1992
- 1992-09-30 GR GR920402178T patent/GR3005844T3/el unknown
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