SE447993B - Forfarande for framstellning av 2,5-bis(2,2,2-trifluoretoxi)-n-(2-piperidylmetyl)bensamid - Google Patents
Forfarande for framstellning av 2,5-bis(2,2,2-trifluoretoxi)-n-(2-piperidylmetyl)bensamidInfo
- Publication number
- SE447993B SE447993B SE8401554A SE8401554A SE447993B SE 447993 B SE447993 B SE 447993B SE 8401554 A SE8401554 A SE 8401554A SE 8401554 A SE8401554 A SE 8401554A SE 447993 B SE447993 B SE 447993B
- Authority
- SE
- Sweden
- Prior art keywords
- bis
- benzamide
- piperidylmethyl
- trifluoroethoxy
- procedure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims description 3
- RHPBLLCTOLJFPH-UHFFFAOYSA-N piperidin-2-ylmethanamine Chemical compound NCC1CCCCN1 RHPBLLCTOLJFPH-UHFFFAOYSA-N 0.000 claims description 3
- DJBNUMBKLMJRSA-UHFFFAOYSA-N Flecainide Chemical compound FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2NCCCC2)=C1 DJBNUMBKLMJRSA-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- RKXNZRPQSOPPRN-UHFFFAOYSA-N flecainide acetate Chemical compound CC(O)=O.FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2NCCCC2)=C1 RKXNZRPQSOPPRN-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YCKWLOJVFNPJAW-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Chemical group FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC=2N=CC=CC=2)=C1 YCKWLOJVFNPJAW-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Natural products CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
15 20 25 30 35 447 993 2 Förfarandet kan genomföras direkt fràn den mättade diamin-2-(aminometyl)piperidinen eller indirekt från 'den oreducerade diamin-2-(aminometyl)pyridinen. Sålunda kan 2-aminometylpiperidin omsättas med 2,5-bis(2,2,2- -trifluoretoxi)-a,a,a-trikloracetofenon eller kan föreningen 2-aminometylpyridin omsättas med trikloraceto- fenonen. I vardera fallet fortskrider reaktionen lätt utan yttre värmning i ett inert lösningsmedel, såsom toluen, bensen, isopropylalkohol, cyklohexan och lik- nande. Reaktionen fortskrider särskilt lätt och med höga utbyten när den oreducerade diaminen omsättes i en blandning av toluen och cyklohexan.
Följande exempel illustrerar förfarandet enligt uppfinningen och är inte avsedda att begränsa uppfin- ningens omfång, sådant det beskrivs ovan.
EXEMPEL 1 Förfarandet genomfört i två reaktioner Till en lösning av 0,05 mol (21,0 g) 2,5-bis-(2,2,2- -trifluoretoxi)-a,d,d-trikloracetofenon i 60 ml toluen ' sättes droppvis en lösning av 0,055 mol (6,0 g) 2-amino- metylpyridin i 50 ml cyklohexan och 10 ml toluen. Reak- tionen är exoterm och en fällning bildas omedelbart.
Ytterligare toluen och cyklohexan tillsättes för att ge en blandningskonsistens som medgör omröring och om- röringen fortsättes i 2 h vid ca 25°C. Fastämnet sepa- reras därefter genom filtrering, tvättas med en bland- ning av toluen och cyklohexan och torkas för att ge ett vitt fastämne. Produkten är 2,5-bis(2,2,2-trifluor- etoxi)-N-(2~pyridylmetyl)bensamid, smp 104-106°C, 17,8 g, 89 % utbyte.
En blandning av 0,33 mol (134,7 g) 2,5-bis(2,2,2- -trifluoretoxi)-N-(2-pyridylmetyl)bensamid, 1,347 liter isättíksyra och 13,5 g 5 % platina på kol reduceras i en Parr-apparat vid ett tryck av 13,6 kp väte vid rums- temperatur. Reaktionen är fullständig på 6-7 h. Reak- tionsblandningen filtreras och katalysatorn tvättas med 10 15 20 447 993 3 isopropylalkohol. Lösningen och tvättvätskorna indunstas för att ge en återstod. Hexan tillsättes till återstoden 'och det resulterande vita fastämnet uppsamlas och om- kristalliseras ur en blandning av aceton och hexan. Ett 71 % utbyte av 2,5-bis(2,2,2-trifluoretoxi)-N-(2-piperir dylmetyl)bensamidacetat, smp 150-l52°C, erhålles. Genom koncentration av den återstående vätskan erhålles ytter- ligare 18% produkt som en andra produktomgàng med en smp av 148-150°C.
EXEMPEL 2 Förfarandet genomfört i en enkelreaktion Till en lösning av 0,01 mol (4,l9 g) 2,5-bis- -(2,2,2-trifluoretoxi)-a,a,a-trikloracetofenon i 50 ml isopropylalkohol sättes 0,01 mol (1,2 g) 2-aminomety1- piperidin. Blandningen blir gradvis fast under en period av 30 min. Blandningen får sätta sig i ca 16 h, varefter 0,01 M ättiksyra och 5 ml isopropylalkohol tillsättes och lösningen värms för att upplösa allt fastämnet. vid kylning erhålles 3,0 g vitt fast ämne. Filtratet indunstas och återstoden omkristalliseras ur isopropyl- alkohol för att ge ytterligare produkt som ett vitt fast ämne. Produkten är 2,S-bis-(2,2,2-trifluoretoxi)- -N-(2-piperidylmetyl)bensamidacetat enligt dess infra- röd- och kärnmagnetíska resonansspektra.
Claims (1)
1. 447 993 PATENTKRAV Förfarande för framställning av 2,5-bis(2,2,2- -trifluoretoxi)-N-(2-piperidylmetyl)bensamid, k ä n - n e t e c k n a t av omsättning av 2,5-bis(2,2,2-tri- fluoretoxi)-a,a,aftrikloracetofenon alternativt med 2-(aminometyl)piperidin för att bilda den önskade pro- dukten i ett steg eller med 2-(aminometyl)pyridin, och därefter reducering för att bilda den önskade pro- dukten, eventuellt som den fria basen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2133279A | 1979-03-19 | 1979-03-19 | |
| US2133179A | 1979-03-19 | 1979-03-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8401554D0 SE8401554D0 (sv) | 1984-03-21 |
| SE8401554L SE8401554L (sv) | 1984-03-21 |
| SE447993B true SE447993B (sv) | 1987-01-12 |
Family
ID=26694559
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8002003A SE447992B (sv) | 1979-03-19 | 1980-03-14 | Forfarande for framstellning av 2,5-bis(2,2,2-trifluoretoxi)-n-(2-piperidylmetyl)bensamid |
| SE8401554A SE447993B (sv) | 1979-03-19 | 1984-03-21 | Forfarande for framstellning av 2,5-bis(2,2,2-trifluoretoxi)-n-(2-piperidylmetyl)bensamid |
| SE8401555A SE463260B (sv) | 1979-03-19 | 1984-03-21 | Acetofenonderivat |
| SE8901533A SE463419B (sv) | 1979-03-19 | 1989-04-27 | Acetofenonderivat |
| SE8901532A SE463418B (sv) | 1979-03-19 | 1989-04-27 | Acetofenonderivat |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8002003A SE447992B (sv) | 1979-03-19 | 1980-03-14 | Forfarande for framstellning av 2,5-bis(2,2,2-trifluoretoxi)-n-(2-piperidylmetyl)bensamid |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8401555A SE463260B (sv) | 1979-03-19 | 1984-03-21 | Acetofenonderivat |
| SE8901533A SE463419B (sv) | 1979-03-19 | 1989-04-27 | Acetofenonderivat |
| SE8901532A SE463418B (sv) | 1979-03-19 | 1989-04-27 | Acetofenonderivat |
Country Status (14)
| Country | Link |
|---|---|
| JP (8) | JPH01125339A (sv) |
| CA (1) | CA1137486A (sv) |
| CH (1) | CH643829A5 (sv) |
| DE (1) | DE3010195A1 (sv) |
| DK (3) | DK167062B1 (sv) |
| ES (1) | ES489629A0 (sv) |
| FR (7) | FR2454438A1 (sv) |
| GB (2) | GB2045760B (sv) |
| IE (1) | IE49558B1 (sv) |
| IL (1) | IL59623A (sv) |
| IT (1) | IT1195262B (sv) |
| NL (1) | NL191486C (sv) |
| PT (1) | PT70967A (sv) |
| SE (5) | SE447992B (sv) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2519979A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylsulfones |
| FR2519980A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de sulfonylation d'halogeno ou trihalogenomethylbenzenes |
| FR2519974A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede d'acylation d'halogeno ou trihalogenomethylbenzenes |
| FR2519975A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylcetones |
| FR2525589A1 (fr) | 1982-04-22 | 1983-10-28 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylcetones |
| FR2525588A1 (fr) * | 1982-04-22 | 1983-10-28 | Rhone Poulenc Spec Chim | Procede de preparation de phenylcetones a partir d'halogeno ou trihalogenomethylbenzenes et de composes aliphatiques ou aromatiques trihalogenomethyles |
| EP0175188A1 (de) * | 1984-09-11 | 1986-03-26 | Nihon Tokushu Noyaku Seizo K.K. | Carbamoylimidazol-Derivate |
| US4675448A (en) * | 1985-02-13 | 1987-06-23 | Ethyl Corporation | Chlorination process |
| FR2579591B1 (fr) * | 1985-03-29 | 1988-10-14 | Rhone Poulenc Spec Chim | Procede de preparation de derives pentafluoroethoxy et pentafluoroethylthiobenzeniques |
| FR2579594B1 (fr) * | 1985-03-29 | 1987-06-05 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoroethoxy ou trifluoroethylthiobenzenes |
| NZ219913A (en) * | 1986-04-25 | 1990-08-28 | Riker Laboratories Inc | Various flecainide derivatives and antibodies raised thereto |
| DE3786037T2 (de) * | 1986-04-25 | 1993-11-25 | Abbott Lab | Tracer zur Benutzung in immunologischen Fluoreszenz-Polarisationsverfahren zum Nachweis von Flecainid. |
| DE3644798A1 (de) * | 1986-12-31 | 1988-07-14 | Hoechst Ag | Neue nitrohaloalkoxybenzole, verfahren zu ihrer herstellung und ihre verwendung |
| FR2640262B1 (fr) * | 1988-12-14 | 1991-05-31 | Rhone Poulenc Chimie | Procede de preparation de cetones aryliques trifluoroethoxylees |
| US6316627B1 (en) | 1997-04-21 | 2001-11-13 | Fine Tech Ltd. | Process for the preparation of flecainide |
| IL120715A (en) | 1997-04-21 | 2000-07-16 | Finetech Ltd | Process for the preparation of (2,2,2,-trifluoroethoxy)benzoic acids |
| IL121288A (en) | 1997-07-11 | 2000-10-31 | Finetech Ltd | Process and a novel intermediate for the preparation of flecainide |
| US7196197B2 (en) | 2003-09-17 | 2007-03-27 | Apotex Pharmachem Inc. | Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof |
| JP4894226B2 (ja) * | 2005-10-31 | 2012-03-14 | Ｄｉｃ株式会社 | ハイドロキノン骨格を有する含フッ素液晶化合物の製造方法 |
| CN117326927A (zh) * | 2023-09-28 | 2024-01-02 | 清源创新实验室 | 一种2,5-双(2,2,2-三氟乙氧基)苯甲酸的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539642A (en) * | 1967-07-19 | 1970-11-10 | Geigy Chem Corp | 2-phenyl-2-(1-naphthyl)acetamides |
| US3772304A (en) * | 1969-10-30 | 1973-11-13 | Hoffmann La Roche | 4-hydroxy-isoquinolines and processes for their preparation |
| US3655728A (en) | 1970-07-22 | 1972-04-11 | Riker Laboratories Inc | N-(2 - dialkylaminoalkylene)-esters of fluoroalkoxy-substituted aryl carboxylic acid and salts thereof |
| US3719687A (en) * | 1970-07-22 | 1973-03-06 | Riker Laboratories Inc | N-(2-dialkylaminoalkylene)amides of 1,1-dihydroperfluoroalkoxy-substituted aryl acids and salts thereof |
| US3967949A (en) * | 1973-06-18 | 1976-07-06 | Eli Lilly And Company | Fluoroalkoxyphenyl-substituted nitrogen heterocycles as plant stunting agents |
| US4169108A (en) * | 1973-08-16 | 1979-09-25 | Sterling Drug Inc. | 5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols |
| US3900481A (en) * | 1974-04-01 | 1975-08-19 | Riker Laboratories Inc | Derivatives of pyrrolidine and piperidine |
| US4005209A (en) * | 1974-04-01 | 1977-01-25 | Riker Laboratories, Inc. | Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides |
| US4013670A (en) * | 1974-04-01 | 1977-03-22 | Riker Laboratories, Inc. | Derivatives of pyrrolidine and piperidine |
| IL49803A (en) * | 1975-06-28 | 1979-11-30 | Fisons Ltd | Preparation of pyrogallol |
| DE2616478C2 (de) * | 1976-04-14 | 1986-05-22 | Brickl, Rolf, Dr., 7951 Warthausen | Fluoracylresorcine enthaltende Arzneimittel, Biocide und Kosmetika |
| JPS6023656B2 (ja) * | 1976-09-02 | 1985-06-08 | 川研フアインケミカル株式会社 | アルコキシ芳香族化合物の製造方法 |
| US4097481A (en) * | 1976-11-08 | 1978-06-27 | Riker Laboratories, Inc. | Tertiary amide derivatives of pyrrolidine and piperidine |
| US4071524A (en) * | 1976-11-08 | 1978-01-31 | Riker Laboratories, Inc. | Derivatives of urea |
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0
- GB GB8214964A patent/GB2097000B/en not_active Expired
-
1980
- 1980-03-04 CA CA000346919A patent/CA1137486A/en not_active Expired
- 1980-03-14 SE SE8002003A patent/SE447992B/sv not_active IP Right Cessation
- 1980-03-14 IL IL59623A patent/IL59623A/xx unknown
- 1980-03-14 DK DK112180A patent/DK167062B1/da not_active IP Right Cessation
- 1980-03-16 NL NL8001551A patent/NL191486C/xx not_active IP Right Cessation
- 1980-03-17 DE DE19803010195 patent/DE3010195A1/de active Granted
- 1980-03-17 ES ES489629A patent/ES489629A0/es active Granted
- 1980-03-18 IE IE549/80A patent/IE49558B1/en not_active IP Right Cessation
- 1980-03-18 PT PT70967A patent/PT70967A/pt active IP Right Revival
- 1980-03-18 CH CH212880A patent/CH643829A5/de not_active IP Right Cessation
- 1980-03-18 FR FR8006019A patent/FR2454438A1/fr active Granted
- 1980-03-18 IT IT20746/80A patent/IT1195262B/it active Protection Beyond IP Right Term
- 1980-03-18 GB GB8009041A patent/GB2045760B/en not_active Expired
-
1981
- 1981-01-07 FR FR8100144A patent/FR2468590A1/fr active Granted
- 1981-01-07 FR FR8100143A patent/FR2468576A1/fr active Granted
- 1981-01-07 FR FR8100142A patent/FR2468571A1/fr active Granted
- 1981-01-07 FR FR8100140A patent/FR2468569A1/fr active Granted
- 1981-01-07 FR FR8100141A patent/FR2468570A1/fr active Granted
- 1981-01-07 FR FR8100145A patent/FR2468591A1/fr active Granted
-
1984
- 1984-03-21 SE SE8401554A patent/SE447993B/sv not_active IP Right Cessation
- 1984-03-21 SE SE8401555A patent/SE463260B/sv not_active IP Right Cessation
-
1988
- 1988-06-01 JP JP63135366A patent/JPH01125339A/ja active Granted
- 1988-06-01 JP JP63135364A patent/JPH01104043A/ja active Granted
- 1988-06-01 JP JP63135365A patent/JPH01104044A/ja active Granted
- 1988-06-01 JP JP63135370A patent/JPH01125344A/ja active Granted
- 1988-06-01 JP JP63135369A patent/JPH01125343A/ja active Granted
- 1988-06-01 JP JP63135368A patent/JPH01125342A/ja active Granted
- 1988-06-01 JP JP63135367A patent/JPH01125341A/ja active Granted
- 1988-06-01 JP JP63135363A patent/JPH01104045A/ja active Granted
-
1989
- 1989-04-27 SE SE8901533A patent/SE463419B/sv not_active IP Right Cessation
- 1989-04-27 SE SE8901532A patent/SE463418B/sv not_active IP Right Cessation
-
1990
- 1990-05-17 DK DK122290A patent/DK164857C/da not_active IP Right Cessation
-
1991
- 1991-04-30 DK DK079891A patent/DK79891A/da unknown
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