CH615914A5 - - Google Patents

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Info

Publication number: CH615914A5
Authority: CH; Switzerland
Prior art keywords: formula; substituted; radical; compounds; group
Prior art date: 1974-02-18

Application number

CH360279A

Other languages

German (de)

English (en)

Inventor

John Lehuep Archibald

John Lambert Jackson

Original Assignee

Wyeth John & Brother Ltd

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.)

1974-02-18

Filing date

1979-04-17

Publication date

1980-02-29

1979-04-17 Application filed by Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd

1980-02-29 Publication of CH615914A5 publication Critical patent/CH615914A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 70
-1 4-phenyl-4-oxobutyl Chemical group 0.000 claims description 51
238000000034 method Methods 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 17
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
150000003053 piperidines Chemical class 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
235000013877 carbamide Nutrition 0.000 claims 3
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
238000003776 cleavage reaction Methods 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims 1
230000007017 scission Effects 0.000 claims 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 claims 1
150000003672 ureas Chemical class 0.000 claims 1
150000003254 radicals Chemical class 0.000 description 16
239000004480 active ingredient Substances 0.000 description 14
239000007787 solid Substances 0.000 description 10
230000000694 effects Effects 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
230000003276 anti-hypertensive effect Effects 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
239000000243 solution Substances 0.000 description 4
GHEFQKHLHFXSBR-UHFFFAOYSA-N 4-chloro-1-phenylbutan-1-one Chemical compound ClCCCC(=O)C1=CC=CC=C1 GHEFQKHLHFXSBR-UHFFFAOYSA-N 0.000 description 3
150000005840 aryl radicals Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
KNNPRHDKYZMBTF-UHFFFAOYSA-N (4-phenylpiperidin-1-yl)urea Chemical class C1CN(NC(=O)N)CCC1C1=CC=CC=C1 KNNPRHDKYZMBTF-UHFFFAOYSA-N 0.000 description 1
DECKKSZJIRXDEJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[1-(4-oxo-4-phenylbutyl)piperidin-4-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1CCN(CCCC(=O)C=2C=CC=CC=2)CC1 DECKKSZJIRXDEJ-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
229920001615 Tragacanth Polymers 0.000 description 1
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical compound [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
AYLIEDQYYJIGDP-UHFFFAOYSA-N [C]1=CC=CS1 Chemical compound [C]1=CC=CS1 AYLIEDQYYJIGDP-UHFFFAOYSA-N 0.000 description 1
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 description 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000839 emulsion Substances 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
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
VDPTZNWSWWZWNC-UHFFFAOYSA-N n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=O)NC1CCNCC1 VDPTZNWSWWZWNC-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
XJVIPPHGDPEDJL-UHFFFAOYSA-N thiourea;hydrochloride Chemical compound Cl.NC(N)=S XJVIPPHGDPEDJL-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- 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
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH360279A 1974-02-18 1979-04-17 CH615914A5 (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB727874A GB1459506A (en)	1974-02-18	1974-02-18	Piperidine derivatives
ZA00754726A ZA754726B (en)	1974-02-18	1975-07-22	Piperidine derivatives

Publications (1)

Publication Number	Publication Date
CH615914A5 true CH615914A5 (fi)	1980-02-29

Family

ID=26241311

Family Applications (3)

Application Number	Title	Priority Date
CH413778A CH612937A5 (fi)	1974-02-18	1975-02-11
CH161075A CH613191A5 (fi)	1974-02-18	1975-02-11
CH360279A CH615914A5 (fi)	1974-02-18	1979-04-17

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CH413778A CH612937A5 (fi)	1974-02-18	1975-02-11
CH161075A CH613191A5 (fi)	1974-02-18	1975-02-11

Country Status (12)

Country	Link
US (1)	US4073790A (fi)
JP (1)	JPS6031825B2 (fi)
BE (1)	BE825458A (fi)
CA (1)	CA1046065A (fi)
CH (3)	CH612937A5 (fi)
DE (1)	DE2505500A1 (fi)
FR (1)	FR2261008B1 (fi)
GB (1)	GB1459506A (fi)
HK (1)	HK57881A (fi)
IN (1)	IN140599B (fi)
NL (1)	NL7501913A (fi)
ZA (1)	ZA754726B (fi)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1561023A (en) *	1977-04-22	1980-02-13	Beecham Group Ltd	2-methoxy - 5 - chloro aniline derivatives
US4281132A (en) *	1977-10-29	1981-07-28	John Wyeth & Brother Limited	Piperidino ureas and thioureas
US4722930A (en) *	1980-03-01	1988-02-02	John Wyeth And Brother Limited	3-benzoyl-1-[(oxo or thioheteroaryl-ylalkyl)-piperid-4-yl]ureas and derivatives
US4806552A (en) *	1980-03-01	1989-02-21	John Wyeth & Brother, Limited	Pyridyl- and/or pyridoyl-(piperid-4-yl) ureas and analogues thereof
ES499716A0 (es) *	1980-03-01	1982-05-01	Wyeth John & Brother Ltd	Un procedimiento para la preparacion de nuevos derivados de piperidina
US4399286A (en) *	1981-07-16	1983-08-16	Mead Johnson & Company	Antiarrhythmic phenethylpiperidine compounds
DE3381799D1 (de) *	1983-09-19	1990-09-13	Bouchara Sa	Substituierte, piperidinoguanidine, verfahren zu ihrer herstellung, und diese enthaltende pharmazeutische zusammensetzungen.
GB8528234D0 (en) *	1985-11-15	1985-12-18	Wyeth John & Brother Ltd	Heterocyclic compounds
US6528529B1 (en) *	1998-03-31	2003-03-04	Acadia Pharmaceuticals Inc.	Compounds with activity on muscarinic receptors
MXPA00009569A (es) *	1998-03-31	2002-08-06	Acadia Pharm Inc	Compuestos con actividad en receptores muscarinicos.
DE19952146A1 (de)	1999-10-29	2001-06-07	Boehringer Ingelheim Pharma	Arylalkane, Arylalkene und Aryl-azaalkane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3238215A (en) *	1963-10-17	1966-03-01	Sterling Drug Inc	1-[(3-, 2-, and 1-indolyl)-lower-alkyl-, lower-alkenyl-, and lower-alkynyl]piperidines
GB1345872A (en) *	1970-09-03	1974-02-06	Wyeth John & Brother Ltd	Amino-and acylamino-pyridine and hydropyridine derivatives

1974
- 1974-02-18 GB GB727874A patent/GB1459506A/en not_active Expired
1975
- 1975-02-10 DE DE19752505500 patent/DE2505500A1/de not_active Ceased
- 1975-02-11 CH CH413778A patent/CH612937A5/xx not_active IP Right Cessation
- 1975-02-11 CH CH161075A patent/CH613191A5/xx not_active IP Right Cessation
- 1975-02-12 US US05/549,271 patent/US4073790A/en not_active Expired - Lifetime
- 1975-02-12 BE BE153297A patent/BE825458A/xx not_active IP Right Cessation
- 1975-02-17 JP JP50019659A patent/JPS6031825B2/ja not_active Expired
- 1975-02-17 FR FR7504834A patent/FR2261008B1/fr not_active Expired
- 1975-02-18 CA CA220,677A patent/CA1046065A/en not_active Expired
- 1975-02-18 NL NL7501913A patent/NL7501913A/xx not_active Application Discontinuation
- 1975-07-22 ZA ZA00754726A patent/ZA754726B/xx unknown
- 1975-07-25 IN IN1449/CAL/75A patent/IN140599B/en unknown
1979
- 1979-04-17 CH CH360279A patent/CH615914A5/de not_active IP Right Cessation
1981
- 1981-11-26 HK HK578/81A patent/HK57881A/xx unknown

Also Published As

Publication number	Publication date
BE825458A (fr)	1975-08-12
ZA754726B (en)	1976-06-30
DE2505500A1 (de)	1975-08-21
NL7501913A (nl)	1975-08-20
JPS50116480A (fi)	1975-09-11
GB1459506A (en)	1976-12-22
HK57881A (en)	1981-12-04
US4073790A (en)	1978-02-14
CA1046065A (en)	1979-01-09
CH612937A5 (fi)	1979-08-31
JPS6031825B2 (ja)	1985-07-24
FR2261008A1 (fi)	1975-09-12
IN140599B (fi)	1976-12-04
CH613191A5 (fi)	1979-09-14
FR2261008B1 (fi)	1978-07-21

Publication	Publication Date	Title
DE2302717A1 (de)	1973-07-26	Heterocyclische verbindungen
EP0053744A1 (de)	1982-06-16	Neue 8-Arylalkyl-3-phenyl-3-nortropanole, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE2012138C3 (de)	1978-08-10	N{4-(ß-Pyrazin- 2-carboxyamido-äthyl)benzolsulphonyl] -N' - cycloalkylharnstoffe und diese enthaltende pharmazeutische Präparate
CH615914A5 (fi)	1980-02-29
EP0163260B1 (de)	1988-08-03	Neue substituierte Pyrrolidinone, Verfahren zu ihrer Herstellung und Arzneimittel
DE2847792C2 (fi)	1988-02-04
DE2816884A1 (de)	1978-11-02	Anilinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2447947A1 (de)	1975-04-17	Indolderivate und verfahren zu ihrer herstellung
DE3216843C2 (de)	1986-10-23	3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0431371B1 (de)	1997-09-10	3-Aminopyrrole, Verfahren zu ihrer Herstellung und ihre Verwendung als Antikonvulsiva
EP0018360B1 (de)	1981-09-30	N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung
DE2617955A1 (de)	1976-11-18	Neue l-substituierte -aroyl-4-hydroxypiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0180115A2 (de)	1986-05-07	1,2,4-Triazolo-carbamate und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
DE2658558A1 (de)	1978-06-29	Diazabicyclo(3,3,1)nonane, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2131034A1 (de)	1973-01-11	Acylharnstoffe und verfahren zu ihrer herstellung
DE3324771A1 (de)	1984-01-12	Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2427272C3 (de)	1981-10-01	1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum
DE2357591C3 (de)	1980-02-28	1 -(4-SuIf amoyIphenyI)-3-phenylimidazolidinone und -dione
EP0003298B1 (de)	1981-03-25	4-Hydroxy-2-benzimidazolin-thion-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
AT339905B (de)	1977-11-10	Verfahren zur herstellung von neuen piperidinderivaten und deren salzen
DE2636866A1 (de)	1977-03-03	Neue phenothiazinderivate und deren herstellung
EP0030343A1 (de)	1981-06-17	Substituierte 2-Amino-3,4-dihydropyridinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2423725A1 (de)	1975-11-27	5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester
DE3886125T2 (de)	1994-06-23	Harnstoff-Derivate.
DE1695092B2 (de)	1978-08-31	N-(4-Sulfonamidophenyl)-a-alkylsuccinimide und deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen

Legal Events

Date	Code	Title	Description
1988-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased