DD142883A5 - Verfahren zur herstellung neuer dithienylalkylhalogenide - Google Patents
Verfahren zur herstellung neuer dithienylalkylhalogenide Download PDFInfo
- Publication number
- DD142883A5 DD142883A5 DD78212127A DD21212778A DD142883A5 DD 142883 A5 DD142883 A5 DD 142883A5 DD 78212127 A DD78212127 A DD 78212127A DD 21212778 A DD21212778 A DD 21212778A DD 142883 A5 DD142883 A5 DD 142883A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- thienyl
- ether
- alk
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 thienyl radical Chemical class 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 241000282979 Alces alces Species 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical compound IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 3
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical group BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001983 dialkylethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- YZSCPLGKKMSBMV-UHFFFAOYSA-N 5-fluoro-4-(8-fluoro-4-propan-2-yl-2,3-dihydro-1,4-benzoxazin-6-yl)-N-[5-(1-methylpiperidin-4-yl)pyridin-2-yl]pyrimidin-2-amine Chemical compound FC=1C(=NC(=NC=1)NC1=NC=C(C=C1)C1CCN(CC1)C)C1=CC2=C(OCCN2C(C)C)C(=C1)F YZSCPLGKKMSBMV-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1121/77A GB1597591A (en) | 1977-01-12 | 1977-01-12 | Dithienyl alkylamines and alkenylamines and a process for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD142883A5 true DD142883A5 (de) | 1980-07-16 |
Family
ID=9716529
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78212127A DD142883A5 (de) | 1977-01-12 | 1978-01-10 | Verfahren zur herstellung neuer dithienylalkylhalogenide |
| DD78203159A DD136265A5 (de) | 1977-01-12 | 1978-01-10 | Verfahren zur herstellung neuer dithienylalkylamine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78203159A DD136265A5 (de) | 1977-01-12 | 1978-01-10 | Verfahren zur herstellung neuer dithienylalkylamine |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US4206213A (enExample) |
| JP (1) | JPS53101362A (enExample) |
| AR (1) | AR227866A1 (enExample) |
| AT (1) | AT362355B (enExample) |
| AU (1) | AU522750B2 (enExample) |
| BE (1) | BE862800A (enExample) |
| CA (1) | CA1096380A (enExample) |
| DD (2) | DD142883A5 (enExample) |
| DE (1) | DE2800535A1 (enExample) |
| DK (1) | DK12478A (enExample) |
| ES (2) | ES465896A1 (enExample) |
| FI (1) | FI780083A7 (enExample) |
| FR (2) | FR2377396A1 (enExample) |
| GB (1) | GB1597591A (enExample) |
| HU (2) | HU178208B (enExample) |
| IN (1) | IN147465B (enExample) |
| NL (1) | NL7800350A (enExample) |
| SE (1) | SE7800326L (enExample) |
| SU (1) | SU747426A3 (enExample) |
| ZA (1) | ZA78174B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275198A (en) * | 1980-07-18 | 1981-06-23 | Carter-Wallace Inc. | Method for preparing basic dithienyl compounds |
| GB9021453D0 (en) * | 1990-10-03 | 1990-11-14 | Wyeth John & Brother Ltd | Piperazine derivatives |
| IT1293804B1 (it) * | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
| US6288083B1 (en) * | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6503926B2 (en) * | 1998-09-04 | 2003-01-07 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US8183390B1 (en) | 2006-07-24 | 2012-05-22 | The United States Of America As Represented By The Secretary Of The Navy | Bis(thienyl)isopyrazoles and process for preparing and method for using bis(thienyl)isopyrazoles |
| US7456295B1 (en) | 2006-11-25 | 2008-11-25 | The United States Of America As Represented By The Secretary Of The Navy | Bis(thienyl)isopyrazoles and process for preparing and method for using bis(thienyl)isopyrazoles |
| US8427812B1 (en) | 2008-07-24 | 2013-04-23 | The United States Of America As Represented By The Secretary Of The Navy | Electroactive polymer based supercapacitors including a cathode having BBL or Pry-BBL |
| EP2447261A1 (en) * | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrole, furane and thiophene derivatives and their use as fungicides |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA497825A (en) | 1953-11-17 | W. Adamson Donald | Preparation of substituted amino-alcohols and derivatives thereof | |
| US2561899A (en) * | 1948-02-25 | 1951-07-24 | Burroughs Wellcome Co | Dithienyl allyl amines |
| GB683977A (en) | 1949-07-18 | 1952-12-10 | Wellcome Found | Improvements in and relating to tertiary amino alkenes |
| GB702847A (en) | 1950-04-28 | 1954-01-27 | Wellcome Found | Process for the preparation of thienyl substituted tertiary amines |
| US3086021A (en) * | 1957-09-20 | 1963-04-16 | Lakeside Lab Inc | Tertiaryamino butynyl alcohols |
| US3002946A (en) * | 1957-11-25 | 1961-10-03 | Dow Corning | Coating composition of polysiloxane resin and two polysiloxane fluids |
| FR1306610A (fr) * | 1960-03-04 | 1962-10-19 | Rech S Mauvernay Lab De | Thiényl-phényl-éthyl (nu-méthylmorpholinium) carbinol, procédé de préparation t applications |
| DE1219038B (de) * | 1962-12-08 | 1966-06-16 | Degussa | Verfahren zur Herstellung von Thiophenverbindungen |
| BE638151A (enExample) | 1963-08-30 | |||
| FR1462206A (fr) * | 1965-06-08 | 1966-04-15 | Innothera Lab Sa | Composés gem-bithiényliques et leur préparation |
| DE1921453C3 (de) * | 1969-04-26 | 1973-04-19 | Degussa | Basische Dithienylderivate |
| FR2103478A2 (en) * | 1970-03-11 | 1972-04-14 | Degussa | 1,1-dithienyl propylamine derivs - for treatment of circulatory disorders |
| SE394280B (sv) * | 1970-04-17 | 1977-06-20 | Degussa | Forfarande for framstellning av basiskt substituerade ditienylderivat |
| US3687945A (en) * | 1970-07-13 | 1972-08-29 | Gold Und Silber Scherdeanstalt | Basic {62 -thienyl compounds |
| US3766173A (en) * | 1970-10-13 | 1973-10-16 | Degussa | Basic dithienyl compounds |
| AT308089B (de) * | 1970-10-14 | 1973-06-25 | Degussa | Verfahren zur Herstellung von neuen Thienylalkanderivaten und ihren Salzen |
| US3826838A (en) * | 1970-10-14 | 1974-07-30 | Degussa | Basic thienylalkanes for increasing blood flow |
| GB1579541A (en) * | 1977-01-12 | 1980-11-19 | Degussa | Process for the production of (1,1 - dithien - (3)-yl - 1 - hydroxy - (3) - propyl) - (1-phenyl - 1 - hydroxy - (2) - propyl)-amine and (1,1 - dithien - (3) - yl-(1) - propen - (3) - yl) - (1 - phenyl-1 - hydroxy - (2) - propyl)- amine |
-
1977
- 1977-01-12 GB GB1121/77A patent/GB1597591A/en not_active Expired
-
1978
- 1978-01-05 US US05/867,157 patent/US4206213A/en not_active Expired - Lifetime
- 1978-01-07 DE DE19782800535 patent/DE2800535A1/de not_active Withdrawn
- 1978-01-10 DD DD78212127A patent/DD142883A5/de unknown
- 1978-01-10 DD DD78203159A patent/DD136265A5/xx unknown
- 1978-01-10 BE BE6046306A patent/BE862800A/xx unknown
- 1978-01-11 AR AR270682A patent/AR227866A1/es active
- 1978-01-11 HU HU78DE949A patent/HU178208B/hu unknown
- 1978-01-11 IN IN35/CAL/78A patent/IN147465B/en unknown
- 1978-01-11 AT AT18978A patent/AT362355B/de not_active IP Right Cessation
- 1978-01-11 FI FI780083A patent/FI780083A7/fi not_active Application Discontinuation
- 1978-01-11 SE SE7800326A patent/SE7800326L/xx unknown
- 1978-01-11 ZA ZA00780174A patent/ZA78174B/xx unknown
- 1978-01-11 ES ES465896A patent/ES465896A1/es not_active Expired
- 1978-01-11 ES ES465897A patent/ES465897A1/es not_active Expired
- 1978-01-11 NL NL7800350A patent/NL7800350A/xx not_active Application Discontinuation
- 1978-01-11 HU HU78DE1033A patent/HU177978B/hu unknown
- 1978-01-11 DK DK12478A patent/DK12478A/da unknown
- 1978-01-11 SU SU782563907A patent/SU747426A3/ru active
- 1978-01-12 FR FR7800792A patent/FR2377396A1/fr active Granted
- 1978-01-12 CA CA294,846A patent/CA1096380A/en not_active Expired
- 1978-01-12 AU AU32392/78A patent/AU522750B2/en not_active Expired
- 1978-01-12 JP JP233378A patent/JPS53101362A/ja active Pending
- 1978-07-03 FR FR7819759A patent/FR2382449A1/fr active Granted
-
1979
- 1979-07-12 US US06/056,838 patent/US4254269A/en not_active Expired - Lifetime
- 1979-07-12 US US06/056,840 patent/US4281010A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53101362A (en) | 1978-09-04 |
| AU522750B2 (en) | 1982-06-24 |
| FR2382449B1 (enExample) | 1982-02-19 |
| US4281010A (en) | 1981-07-28 |
| HU177978B (en) | 1982-02-28 |
| FR2382449A1 (fr) | 1978-09-29 |
| FR2377396A1 (fr) | 1978-08-11 |
| DK12478A (da) | 1978-07-13 |
| NL7800350A (nl) | 1978-07-14 |
| ES465896A1 (es) | 1978-09-16 |
| US4206213A (en) | 1980-06-03 |
| US4254269A (en) | 1981-03-03 |
| AR227866A1 (es) | 1982-12-30 |
| HU178208B (en) | 1982-03-28 |
| ES465897A1 (es) | 1978-09-16 |
| SE7800326L (sv) | 1978-07-13 |
| FR2377396B1 (enExample) | 1982-05-07 |
| GB1597591A (en) | 1981-09-09 |
| IN147465B (enExample) | 1980-03-08 |
| DD136265A5 (de) | 1979-06-27 |
| AU3239278A (en) | 1979-07-19 |
| ZA78174B (en) | 1978-11-29 |
| AT362355B (de) | 1981-05-11 |
| ATA18978A (de) | 1980-10-15 |
| BE862800A (fr) | 1978-07-10 |
| CA1096380A (en) | 1981-02-24 |
| DE2800535A1 (de) | 1978-07-13 |
| SU747426A3 (ru) | 1980-07-23 |
| FI780083A7 (fi) | 1978-07-13 |
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