NO126319B - - Google Patents

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Info

Publication number: NO126319B
Authority: NO; Norway
Prior art keywords: denotes; formula; fluorobenzoyl; propyl; hydrogen
Prior art date: 1967-01-16

Application number

NO00159/68A

Other languages

English (en)

Norwegian (no)

Inventor

John Hans Biel

Jorge Pengman Li

Robert George Stein

John Fred Hoops

Original Assignee

Aldrich Chem Co Inc

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.)

1967-01-16

Filing date

1968-01-15

Publication date

1973-01-22

1968-01-15 Application filed by Aldrich Chem Co Inc filed Critical Aldrich Chem Co Inc

1973-01-22 Publication of NO126319B publication Critical patent/NO126319B/no

Links

150000001875 compounds Chemical class 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
238000000034 method Methods 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
150000003053 piperidines Chemical class 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 8
OJTNFBDLVWOHKM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-hydroxypiperidin-1-yl)butan-1-one Chemical compound C1CC(O)CCN1CCCC(=O)C1=CC=C(F)C=C1 OJTNFBDLVWOHKM-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
-1 ^£00^ Chemical class 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000007787 solid Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HGONUOPZUMDLIA-UHFFFAOYSA-N Cl.ClC(=O)OC1CCN(CC1)CCCC(C1=CC=C(C=C1)F)=O Chemical compound Cl.ClC(=O)OC1CCN(CC1)CCCC(C1=CC=C(C=C1)F)=O HGONUOPZUMDLIA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
DLLRHKHMDMRZFE-UHFFFAOYSA-N 1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol Chemical compound C1OC(CCCN2CCC(CC2)O)(C2=CC=C(C=C2)F)OC1 DLLRHKHMDMRZFE-UHFFFAOYSA-N 0.000 description 2
FXFDJSQOCVDXBX-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane Chemical compound C1=CC(F)=CC=C1C1(CCCCl)OCCO1 FXFDJSQOCVDXBX-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HJSFDYCHYVGVDC-UHFFFAOYSA-N [1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] n-propan-2-ylcarbamate Chemical compound C1CC(OC(=O)NC(C)C)CCN1CCCC(=O)C1=CC=C(F)C=C1 HJSFDYCHYVGVDC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 2
IGWCIHCQFSETGG-UHFFFAOYSA-N carbonochloridic acid;hydron;chloride Chemical compound Cl.OC(Cl)=O IGWCIHCQFSETGG-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229940125723 sedative agent Drugs 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MBNBAODMHRPUKN-UHFFFAOYSA-N 2-fluoro-1-phenylbutan-1-one Chemical compound CCC(F)C(=O)C1=CC=CC=C1 MBNBAODMHRPUKN-UHFFFAOYSA-N 0.000 description 1
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 description 1
RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101100083446 Danio rerio plekhh1 gene Proteins 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
206010020772 Hypertension Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229960005222 phenazone Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect 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
230000007306 turnover Effects 0.000 description 1
238000005303 weighing 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
- C07D211/36—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 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 to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO00159/68A 1967-01-16 1968-01-15 NO126319B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60933967A	1967-01-16	1967-01-16

Publications (1)

Publication Number	Publication Date
NO126319B true NO126319B (fr)	1973-01-22

Family

ID=24440375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00159/68A NO126319B (fr)	1967-01-16	1968-01-15

Country Status (12)

Country	Link
US (1)	US3484446A (fr)
AT (1)	AT275516B (fr)
BE (1)	BE709445A (fr)
CH (1)	CH495357A (fr)
DE (1)	DE1670020C3 (fr)
ES (1)	ES349326A1 (fr)
FR (2)	FR1572213A (fr)
GB (1)	GB1215379A (fr)
IL (1)	IL29262A (fr)
NL (1)	NL6800647A (fr)
NO (1)	NO126319B (fr)
SE (1)	SE342224B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0017478B1 (fr) *	1979-04-05	1983-03-30	BEECHAM - WUELFING GmbH & Co. KG	Dialkoxy- et dioxacycloalkyl-alkylthéobromines, compositions pharmaceutiques les contenant et leur préparation
IL59664A0 (en) *	1979-04-05	1980-06-30	Wuelfing J Kg	Xanthine derivatives,process for their preparation and their use in pharmaceutical compositions
US4283404A (en) *	1979-09-04	1981-08-11	Richardson-Merrell Inc.	Aroylethenylpiperidinobutyrophenone antipsychotic agents
US4284636A (en) *	1979-09-04	1981-08-18	Richardson-Merrell Inc.	Cinnamoylpiperidinobutyrophenone antipsychotic agents
US4810792A (en) *	1987-01-22	1989-03-07	Hoechst-Roussel Pharmaceuticals Inc.	Piperidine intermediates

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1459A (fr) *	1901-10-12
NL110185C (fr) *	1958-04-22
US3031455A (en) *	1959-07-20	1962-04-24	Upjohn Co	1-phenethyl-4-piperidyl carbamates
US3161637A (en) *	1961-10-10	1964-12-15	Res Lab Dr C Janssen N V	1-(gamma-aroyl-propyl)-4-(nu-arylcarbonyl amino) piperidines and related compounds
GB1029220A (en) *	1963-07-29	1966-05-11	Ferrosan Ab	Basic ketone compounds and a process for their production
CH437285A (de) *	1964-03-09	1967-06-15	Geigy Ag J R	Verfahren zur Herstellung von neuen Pyrrolidin-, Piperidin- und Azepinderivaten

1967
- 1967-01-16 US US609339A patent/US3484446A/en not_active Expired - Lifetime
1968
- 1968-01-03 IL IL29262A patent/IL29262A/en unknown
- 1968-01-10 DE DE1670020A patent/DE1670020C3/de not_active Expired
- 1968-01-15 NO NO00159/68A patent/NO126319B/no unknown
- 1968-01-15 GB GB2159/68A patent/GB1215379A/en not_active Expired
- 1968-01-15 SE SE453/68A patent/SE342224B/xx unknown
- 1968-01-15 ES ES349326A patent/ES349326A1/es not_active Expired
- 1968-01-16 CH CH65968A patent/CH495357A/de not_active IP Right Cessation
- 1968-01-16 NL NL6800647A patent/NL6800647A/xx unknown
- 1968-01-16 AT AT45668A patent/AT275516B/de active
- 1968-01-16 FR FR1572213D patent/FR1572213A/fr not_active Expired
- 1968-01-16 BE BE709445D patent/BE709445A/xx unknown
- 1968-03-29 FR FR146183A patent/FR7390M/fr not_active Expired

Also Published As

Publication number	Publication date
DE1670020A1 (de)	1972-03-30
ES349326A1 (es)	1969-09-16
CH495357A (de)	1970-08-31
FR1572213A (fr)	1969-06-27
NL6800647A (fr)	1968-07-17
SE342224B (fr)	1972-01-31
AT275516B (de)	1969-10-27
FR7390M (fr)	1969-10-27
IL29262A (en)	1971-11-29
DE1670020C3 (de)	1974-06-12
BE709445A (fr)	1968-07-16
US3484446A (en)	1969-12-16
GB1215379A (en)	1970-12-09
DE1670020B2 (de)	1973-11-08

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JPH075539B2 (ja)	1995-01-25	置換スルホンアミドベンズアミド及びその製法
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