NO123245B - - Google Patents
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- Publication number
- NO123245B NO123245B NO16839667A NO16839667A NO123245B NO 123245 B NO123245 B NO 123245B NO 16839667 A NO16839667 A NO 16839667A NO 16839667 A NO16839667 A NO 16839667A NO 123245 B NO123245 B NO 123245B
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- benzhydryl
- ethyl
- hydroxyethoxy
- boiling point
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical class C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 6
- 238000012986 modification Methods 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 127
- 238000009835 boiling Methods 0.000 description 49
- -1 1-p-bromobenzhydryl-4-[2-(2-hydroxyethoxy)-ethyl]-piperazine Chemical compound 0.000 description 41
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 239000002585 base Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229960005141 piperazine Drugs 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RMXZOOYQUFHRPE-UHFFFAOYSA-N 1-[(4-bromophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 RMXZOOYQUFHRPE-UHFFFAOYSA-N 0.000 description 3
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 3
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- KECMLGZOQMJIBM-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCCl KECMLGZOQMJIBM-UHFFFAOYSA-N 0.000 description 2
- GYCLKODXTAIUAY-UHFFFAOYSA-N 2-[2-(2-piperazin-1-ylethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCN1CCNCC1 GYCLKODXTAIUAY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical class OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FLNQAPQQAZVRDA-UHFFFAOYSA-N 1-(2-(2-Hydroxyethoxy)ethyl)piperazine Chemical compound OCCOCCN1CCNCC1 FLNQAPQQAZVRDA-UHFFFAOYSA-N 0.000 description 1
- YMXAYMSJCVGYEM-UHFFFAOYSA-N 1-Chloro-2-(chlorophenylmethyl)benzene Chemical compound C=1C=CC=C(Cl)C=1C(Cl)C1=CC=CC=C1 YMXAYMSJCVGYEM-UHFFFAOYSA-N 0.000 description 1
- JHKFGCFYIKPSJX-UHFFFAOYSA-N 1-[(2-bromophenyl)-phenylmethyl]piperazine Chemical compound BrC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 JHKFGCFYIKPSJX-UHFFFAOYSA-N 0.000 description 1
- RLZPNIGECDMAJH-UHFFFAOYSA-N 1-[(2-chlorophenyl)-phenylmethyl]piperazine Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 RLZPNIGECDMAJH-UHFFFAOYSA-N 0.000 description 1
- IZNRYBFUKJNNLH-UHFFFAOYSA-N 1-[(2-methylphenyl)-phenylmethyl]piperazine Chemical compound CC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 IZNRYBFUKJNNLH-UHFFFAOYSA-N 0.000 description 1
- YNZQUVOSFLCDGV-UHFFFAOYSA-N 1-[(3-bromophenyl)-phenylmethyl]piperazine Chemical compound BrC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 YNZQUVOSFLCDGV-UHFFFAOYSA-N 0.000 description 1
- UGTBQURRNOQZSV-UHFFFAOYSA-N 1-[(3-chlorophenyl)-phenylmethyl]piperazine Chemical compound ClC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 UGTBQURRNOQZSV-UHFFFAOYSA-N 0.000 description 1
- KMXMAWICRXKQFE-UHFFFAOYSA-N 1-[(3-methoxyphenyl)-phenylmethyl]piperazine Chemical compound COC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 KMXMAWICRXKQFE-UHFFFAOYSA-N 0.000 description 1
- JYNPNQFAXHCTBV-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-3-methoxybenzene Chemical compound COC1=CC=CC(C(Cl)C=2C=CC=CC=2)=C1 JYNPNQFAXHCTBV-UHFFFAOYSA-N 0.000 description 1
- CFPYBVHEZBNWTR-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-3-methylbenzene Chemical compound CC1=CC=CC(C(Cl)C=2C=CC=CC=2)=C1 CFPYBVHEZBNWTR-UHFFFAOYSA-N 0.000 description 1
- GHBNCXLSRVICCO-UHFFFAOYSA-N 1-bromo-2-[chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=C(Br)C=1C(Cl)C1=CC=CC=C1 GHBNCXLSRVICCO-UHFFFAOYSA-N 0.000 description 1
- DNRHPNFMEIEGMA-UHFFFAOYSA-N 1-bromo-3-[chloro(phenyl)methyl]benzene Chemical compound C=1C=CC(Br)=CC=1C(Cl)C1=CC=CC=C1 DNRHPNFMEIEGMA-UHFFFAOYSA-N 0.000 description 1
- NOMHRYCAVGPGEC-UHFFFAOYSA-N 1-bromo-4-[chloro(phenyl)methyl]benzene Chemical compound C=1C=C(Br)C=CC=1C(Cl)C1=CC=CC=C1 NOMHRYCAVGPGEC-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VUFOCTSXHUWGPW-UHFFFAOYSA-N etodroxizine Chemical compound C1CN(CCOCCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 VUFOCTSXHUWGPW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003506 piperazine hexahydrate Drugs 0.000 description 1
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Graft Or Block Polymers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55468366A | 1966-06-02 | 1966-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123245B true NO123245B (de) | 1971-10-18 |
Family
ID=24214293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16839667A NO123245B (de) | 1966-06-02 | 1967-05-31 |
Country Status (7)
| Country | Link |
|---|---|
| BR (1) | BR6790060D0 (de) |
| CH (1) | CH553836A (de) |
| DE (1) | DE1694973C3 (de) |
| GB (1) | GB1169605A (de) |
| IL (1) | IL27997A (de) |
| NO (1) | NO123245B (de) |
| SE (1) | SE354475B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030195A1 (de) * | 1980-08-09 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Bei raumtemperatur vernetzbare pfropfpolymerisat-dispersionen |
| DE3105499A1 (de) * | 1981-02-14 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Stabile, organische mehrkomponentendispersionen |
| US4797501A (en) * | 1986-12-31 | 1989-01-10 | Union Carbide Corporation | Silicone-based stabilizers useful in the preparation of improved polyurethane foams |
| DE102006059295B4 (de) * | 2006-12-11 | 2009-12-17 | Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh | Hydrolysierte silangepfropfte Olefinhomo- und(block)copolymere sowie Verfahren zu ihrer Herstellung |
| CN102964983B (zh) * | 2012-12-12 | 2015-01-07 | 广州市高士实业有限公司 | 一种硅杂化复合涂覆电子胶及其制备方法 |
-
1967
- 1967-05-17 IL IL2799767A patent/IL27997A/en unknown
- 1967-05-24 GB GB2408167A patent/GB1169605A/en not_active Expired
- 1967-05-31 NO NO16839667A patent/NO123245B/no unknown
- 1967-06-01 BR BR19006067A patent/BR6790060D0/pt unknown
- 1967-06-01 DE DE19671694973 patent/DE1694973C3/de not_active Expired
- 1967-06-02 SE SE775067A patent/SE354475B/xx unknown
- 1967-06-02 CH CH782667A patent/CH553836A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH553836A (de) | 1974-09-13 |
| DE1694973A1 (de) | 1971-12-30 |
| IL27997A (en) | 1971-07-28 |
| GB1169605A (en) | 1969-11-05 |
| DE1694973C3 (de) | 1975-05-07 |
| BR6790060D0 (pt) | 1973-01-16 |
| DE1694973B2 (de) | 1974-09-05 |
| SE354475B (de) | 1973-03-12 |
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