FI67537C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya 1,2-bis-dialkylaminoetoxi-3-fenoxipropaner - Google Patents

Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya 1,2-bis-dialkylaminoetoxi-3-fenoxipropaner Download PDF

Info

Publication number: FI67537C
Authority: FI; Finland
Prior art keywords: formula; bis; compound; chlorine; salt
Prior art date: 1976-07-19

Application number

FI772105A

Other languages

English (en)

Finnish (fi)

Other versions

FI772105A (ja

FI67537B (fi

Inventor

Francois Molnar

Suzanne Szabo

Peter Radanow Statkov

Original Assignee

Cermos Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-07-19

Filing date

1977-07-05

Publication date

1985-04-10

1977-07-05 Application filed by Cermos Sa filed Critical Cermos Sa

1978-01-20 Publication of FI772105A publication Critical patent/FI772105A/fi

1984-12-31 Application granted granted Critical

1984-12-31 Publication of FI67537B publication Critical patent/FI67537B/fi

1985-04-10 Publication of FI67537C publication Critical patent/FI67537C/fi

Links

230000000144 pharmacologic effect Effects 0.000 title description 2
230000035764 nutrition Effects 0.000 title 1
235000016709 nutrition Nutrition 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 10
239000002585 base Substances 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
125000005336 allyloxy group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
-1 methoxyethyl Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000002366 halogen compounds Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
HQGGIYPCJYWTHA-UHFFFAOYSA-N 1-[3-(2-methoxyphenoxy)propoxy]-n,n,n',n'-tetramethylethane-1,2-diamine Chemical compound COC1=CC=CC=C1OCCCOC(CN(C)C)N(C)C HQGGIYPCJYWTHA-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
AXOFLJQULKZRCV-UHFFFAOYSA-N n,n,n',n'-tetraethyl-1-[3-(2-methoxyphenoxy)propoxy]ethane-1,2-diamine Chemical compound CCN(CC)CC(N(CC)CC)OCCCOC1=CC=CC=C1OC AXOFLJQULKZRCV-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
229960004194 lidocaine Drugs 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
206010003119 arrhythmia Diseases 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical compound OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000006793 arrhythmia Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 3
XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
229940039750 aconitine Drugs 0.000 description 3
STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
CJDRUOGAGYHKKD-RQBLFBSQSA-N 1pon08459r Chemical compound CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O CJDRUOGAGYHKKD-RQBLFBSQSA-N 0.000 description 2
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
244000061121 Rauvolfia serpentina Species 0.000 description 2
229960004332 ajmaline Drugs 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
RKBUSASMODUQSK-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propane-1,2,3-triol Chemical compound CC1=C(OC(O)C(O)CO)C(=CC=C1)C RKBUSASMODUQSK-UHFFFAOYSA-N 0.000 description 1
YFBMUIMQJYESPZ-UHFFFAOYSA-N 3-phenoxy-1,2-propanediol Natural products C1C(OC(C)=O)CCC2(C)C3=CCC4(C)C(C(C)CCC(CC)C(C)C)CCC4(C)C3CCC21 YFBMUIMQJYESPZ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
SSXJLINCRCPTIS-UHFFFAOYSA-N C(C)N(C(COCC)(COC1=C(C=CC=C1)OC)O)CC Chemical compound C(C)N(C(COCC)(COC1=C(C=CC=C1)OC)O)CC SSXJLINCRCPTIS-UHFFFAOYSA-N 0.000 description 1
ACZRWOJGUAAIMN-UHFFFAOYSA-N C(CC)C1=CC=CC=C1.C(C=C/C(=O)O)(=O)O Chemical compound C(CC)C1=CC=CC=C1.C(C=C/C(=O)O)(=O)O ACZRWOJGUAAIMN-UHFFFAOYSA-N 0.000 description 1
208000020446 Cardiac disease Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
JHWQMXKQJVAWKI-UHFFFAOYSA-N UNPD187286 Natural products OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
238000002690 local anesthesia Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960005010 orotic acid Drugs 0.000 description 1
239000001294 propane Substances 0.000 description 1
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
210000003497 sciatic nerve Anatomy 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
ZBIISBRWGXZJKH-UHFFFAOYSA-N sodium;1-(diethylamino)ethanolate Chemical compound [Na+].CCN(CC)C(C)[O-] ZBIISBRWGXZJKH-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Emergency Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI772105A 1976-07-19 1977-07-05 Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya 1,2-bis-dialkylaminoetoxi-3-fenoxipropaner FI67537C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH921776		1976-07-19
CH921776A CH602581A5 (ja)	1976-07-19	1976-07-19

Publications (3)

Publication Number	Publication Date
FI772105A FI772105A (ja)	1978-01-20
FI67537B FI67537B (fi)	1984-12-31
FI67537C true FI67537C (fi)	1985-04-10

Family

ID=4349615

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI772105A FI67537C (fi)	1976-07-19	1977-07-05	Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya 1,2-bis-dialkylaminoetoxi-3-fenoxipropaner

Country Status (17)

Country	Link
US (1)	US4117160A (ja)
JP (1)	JPS5312828A (ja)
AT (1)	AT349447B (ja)
AU (1)	AU2706077A (ja)
BE (1)	BE856258A (ja)
CA (1)	CA1095085A (ja)
CH (1)	CH602581A5 (ja)
DE (1)	DE2728315A1 (ja)
DK (1)	DK158463C (ja)
ES (1)	ES460825A1 (ja)
FI (1)	FI67537C (ja)
FR (1)	FR2359118A1 (ja)
GB (1)	GB1572370A (ja)
NL (1)	NL187909C (ja)
NZ (1)	NZ184647A (ja)
SE (1)	SE429755B (ja)
ZA (1)	ZA774155B (ja)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7799337B2 (en)	1997-07-21	2010-09-21	Levin Bruce H	Method for directed intranasal administration of a composition
US8473062B2 (en)	2008-05-01	2013-06-25	Autonomic Technologies, Inc.	Method and device for the treatment of headache
US8412336B2 (en)	2008-12-29	2013-04-02	Autonomic Technologies, Inc.	Integrated delivery and visualization tool for a neuromodulation system
US9320908B2 (en)	2009-01-15	2016-04-26	Autonomic Technologies, Inc.	Approval per use implanted neurostimulator
US8494641B2 (en)	2009-04-22	2013-07-23	Autonomic Technologies, Inc.	Implantable neurostimulator with integral hermetic electronic enclosure, circuit substrate, monolithic feed-through, lead assembly and anchoring mechanism

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2738351A (en) *	1952-08-02	1956-03-13	Bristol Lab Inc	Substituted glycerol ethers
US2895995A (en) *	1957-04-10	1959-07-21	Willey George Lawrence	Quaternary ammonium salts of dialkylaminoalkyl phenyl ethers
GB1262785A (en) *	1969-04-29	1972-02-09	Orsymonde	Improvements in or relating to phloroglucinol derivatives
FR2146893B1 (ja) *	1971-07-23	1974-09-06	Crt
DE2431126A1 (de) *	1974-06-28	1976-01-15	Christian Brunnengraeber Chem	Therapeutikum mit antiarrhythischer wirkung

1976
- 1976-07-19 CH CH921776A patent/CH602581A5/xx not_active IP Right Cessation
1977
- 1977-06-23 DE DE19772728315 patent/DE2728315A1/de active Granted
- 1977-06-27 NL NLAANVRAGE7707088,A patent/NL187909C/xx active Search and Examination
- 1977-06-27 GB GB26786/77A patent/GB1572370A/en not_active Expired
- 1977-06-29 BE BE178897A patent/BE856258A/xx not_active IP Right Cessation
- 1977-07-05 FI FI772105A patent/FI67537C/fi not_active IP Right Cessation
- 1977-07-08 US US05/813,985 patent/US4117160A/en not_active Expired - Lifetime
- 1977-07-11 CA CA282,474A patent/CA1095085A/en not_active Expired
- 1977-07-11 ZA ZA00774155A patent/ZA774155B/xx unknown
- 1977-07-12 FR FR7721561A patent/FR2359118A1/fr active Granted
- 1977-07-14 NZ NZ184647A patent/NZ184647A/xx unknown
- 1977-07-15 AU AU27060/77A patent/AU2706077A/en active Pending
- 1977-07-16 ES ES460825A patent/ES460825A1/es not_active Expired
- 1977-07-18 AT AT516677A patent/AT349447B/de not_active IP Right Cessation
- 1977-07-18 SE SE7708299A patent/SE429755B/xx not_active IP Right Cessation
- 1977-07-18 DK DK324577A patent/DK158463C/da not_active IP Right Cessation
- 1977-07-19 JP JP8657977A patent/JPS5312828A/ja active Granted

Also Published As

Publication number	Publication date
DK158463C (da)	1990-10-08
NL7707088A (nl)	1978-01-23
ATA516677A (de)	1978-09-15
DE2728315A1 (de)	1978-01-26
ES460825A1 (es)	1978-04-16
CA1095085A (en)	1981-02-03
GB1572370A (en)	1980-07-30
NZ184647A (en)	1979-12-11
NL187909C (nl)	1992-02-17
FI772105A (ja)	1978-01-20
FR2359118A1 (fr)	1978-02-17
DE2728315C2 (ja)	1987-01-22
JPS6228776B2 (ja)	1987-06-23
US4117160A (en)	1978-09-26
BE856258A (fr)	1977-10-17
SE7708299L (sv)	1978-01-20
DK158463B (da)	1990-05-21
SE429755B (sv)	1983-09-26
FR2359118B1 (ja)	1979-05-11
AT349447B (de)	1979-04-10
CH602581A5 (ja)	1978-07-31
AU2706077A (en)	1979-01-18
JPS5312828A (en)	1978-02-04
ZA774155B (en)	1978-05-30
DK324577A (da)	1978-01-20
FI67537B (fi)	1984-12-31

Legal Events

Date	Code	Title	Description
1993-07-05	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: CERMOL SA

Publication	Publication Date	Title
FI71126B (fi)	1986-08-14	Foerfarande foer framstaellning av n-(1-alkyl- eller allyl-2-pyrrolidinylmetyl)-2-metoxi-4-amino-5-alkylsulfonylbensamider
US4076820A (en)	1978-02-28	Benzoquinolizines and hypotensive compositions containing them
US4059621A (en)	1977-11-22	Substituted benzamido propanolamines
US4730042A (en)	1988-03-08	Compounds 1 or 3-hydroxy-4-benzyl-6-methyl-7-(4-isopropylamino-butoxy)-1,3-dihydro[3,4-C]pyridine and 2-methyl-3-(4-isopropyl-aminobutoxy)-4-(1'-morphilinomethyl)-5-hydroxymethyl-6-benzyl pyridine, useful for treating cardiac arrhythmias
US4575508A (en)	1986-03-11	2-Substituted 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-β-carbolines, and their use as antiarrhythmic agents
EP0132764B1 (en)	1991-01-02	Derivatives of dihydrodibenzocycloheptylidene-ethylamine
GB2046259A (en)	1980-11-12	Amino-alcohol derivatives and pharmaceutical compositions containing them
US4278796A (en)	1981-07-14	Piperazines
FI67537C (fi)	1985-04-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya 1,2-bis-dialkylaminoetoxi-3-fenoxipropaner
NO155880B (no)	1987-03-09	Analogifremgangsmaate til fremstilling av terapeutisk aktivt 2-(2'hydroksy-3'-(1,1-dimetylpropylamino)-propoksy)-beta-fenylpropionfenon.
FI57259C (fi)	1980-07-10	Foerfarande foer framstaellning av bronkolytiska och sekretolytiska 6,11-dihydro-6-metyl-5h-pyrido/2,3-b//1,5/benzodiazepin-5-oner och 5,11-dihydro-5-metyl-6h-pyrido/2,3-b//1,4/benzodiazepin-6-oner
FI77456B (fi)	1988-11-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-/2-/4-(2-metoxifenyl) -1-piperazinyl/etyl/-2,4-(1h,3h)-kinazolindionderivat.
US3200151A (en)	1965-08-10	Arylaminoalkyl guanidines
US4550111A (en)	1985-10-29	Alkanolamine derivatives
US3726900A (en)	1973-04-10	Dibenzo(a-d)cycloheptadi(or tri)ene-5:2'-dioxalanes(i,3')
FI64145B (fi)	1983-06-30	Foerfarande foer framstaellning av 2-arylamino-2-imidazolinderivat
US4315939A (en)	1982-02-16	Piperidine derivatives of 4,5-dialkyl-3-hydroxy-pyrrole-2-carboxylic acid esters, pharmaceutical formulations containing these compounds and use in treating cardiac arrhythmias
FI62086B (fi)	1982-07-30	Foerfarande foer framstaellning av bronkosekreterolytiska 5,11-dihydro-5h-pyrido-(2,3-b)(1,5)bensodiazepin-5-oner
US4086361A (en)	1978-04-25	Aminoethyl oximes having anti-depressive activity
US4438121A (en)	1984-03-20	Isoquinoline amidoxime derivatives
US3717637A (en)	1973-02-20	TRIFLUOROMETHYLTHIO SUBSTITUTED DIBENZ [b,f] [1,4] OXAZEPINES
CS196399B2 (en)	1980-03-31	Process for preparing 2-substituted 1-/omega-amino-alkoxy/-benzenes
IE50035B1 (en)	1986-02-05	Hexahydro-trans-pyridoindole neuroleptic agents
US3337538A (en)	1967-08-22	Noyel homopiperazine alkyl substituted iminostilbene compounds
GB2106516A (en)	1983-04-13	Anthranilic acid esters