CH618970A5 - Process for the preparation of 4-amido-trans-decahydroquinoline derivatives - Google Patents

Process for the preparation of 4-amido-trans-decahydroquinoline derivatives Download PDF

Info

Publication number: CH618970A5
Authority: CH; Switzerland
Prior art keywords: trans; decahydroquinoline; amino; phenyl; propyl
Prior art date: 1975-12-16

Application number

CH1565976A

Other languages

English (en)

French (fr)

Inventor

Maurice Prost

Original Assignee

Labaz

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.)

1975-12-16

Filing date

1976-12-13

Publication date

1980-08-29

1976-12-13 Application filed by Labaz filed Critical Labaz

1980-08-29 Publication of CH618970A5 publication Critical patent/CH618970A5/fr

Links

238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 76
239000002253 acid Substances 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical class 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000002541 furyl group Chemical group 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
150000008064 anhydrides Chemical class 0.000 claims abstract 2
-1 carbonyl-hydrazono Chemical group 0.000 claims description 88
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 76
POTIYWUALSJREP-DTWKUNHWSA-N (4as,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCC[C@@H]2CCCC[C@H]21 POTIYWUALSJREP-DTWKUNHWSA-N 0.000 claims description 74
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
238000010992 reflux Methods 0.000 claims description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000002723 alicyclic group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
125000003375 sulfoxide group Chemical group 0.000 claims 1
POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical class N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 abstract description 5
239000000730 antalgic agent Substances 0.000 abstract description 4
239000002220 antihypertensive agent Substances 0.000 abstract description 4
229940030600 antihypertensive agent Drugs 0.000 abstract description 3
229940035676 analgesics Drugs 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
150000003335 secondary amines Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 41
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 31
241001465754 Metazoa Species 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
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239000000203 mixture Substances 0.000 description 17
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 10
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CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000003276 anti-hypertensive effect Effects 0.000 description 6
229960005181 morphine Drugs 0.000 description 6
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 6
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 5
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
208000002193 Pain Diseases 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000036407 pain Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 4
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960001138 acetylsalicylic acid Drugs 0.000 description 4
VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 4
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238000001953 recrystallisation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 3
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
239000007864 aqueous solution Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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QALFFERHOHJEGF-KUARMEPBSA-N Cl.N1([C@@H]2CCCC[C@H]2CCC1)CC(=O)C1=CC=CC=C1 Chemical compound Cl.N1([C@@H]2CCCC[C@H]2CCC1)CC(=O)C1=CC=CC=C1 QALFFERHOHJEGF-KUARMEPBSA-N 0.000 description 2
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IPKWXEINWYUTQF-UHFFFAOYSA-N butan-2-one;hexane Chemical compound CCC(C)=O.CCCCCC IPKWXEINWYUTQF-UHFFFAOYSA-N 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
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229960001650 glafenine Drugs 0.000 description 2
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238000007912 intraperitoneal administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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230000029058 respiratory gaseous exchange Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
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238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002005 ganglioplegic effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 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
229960001027 opium Drugs 0.000 description 1
230000037040 pain threshold Effects 0.000 description 1
238000010422 painting Methods 0.000 description 1
206010033675 panniculitis Diseases 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008063 pharmaceutical solvent Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000000194 sympathicotonic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4

Landscapes

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

CH1565976A 1975-12-16 1976-12-13 Process for the preparation of 4-amido-trans-decahydroquinoline derivatives CH618970A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB51507/75A GB1515540A (en)	1975-12-16	1975-12-16	4-amino-trans-decahydroquinoline derivatives

Publications (1)

Publication Number	Publication Date
CH618970A5 true CH618970A5 (en)	1980-08-29

Family

ID=10460296

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1565976A CH618970A5 (en)	1975-12-16	1976-12-13	Process for the preparation of 4-amido-trans-decahydroquinoline derivatives

Country Status (28)

Country	Link
JP (1)	JPS6022711B2 (pl)
AR (1)	AR214988A1 (pl)
AT (1)	AT357535B (pl)
AU (1)	AU509897B2 (pl)
BE (1)	BE849431A (pl)
CA (1)	CA1077040A (pl)
CH (1)	CH618970A5 (pl)
DD (1)	DD128709A5 (pl)
DE (1)	DE2656678C2 (pl)
DK (1)	DK564876A (pl)
ES (1)	ES454285A1 (pl)
FI (1)	FI63023C (pl)
FR (1)	FR2335224A1 (pl)
GB (1)	GB1515540A (pl)
HU (1)	HU175391B (pl)
IE (1)	IE44355B1 (pl)
IT (1)	IT1065969B (pl)
MX (1)	MX5798E (pl)
NL (1)	NL7613629A (pl)
NO (1)	NO145916C (pl)
NZ (1)	NZ182758A (pl)
OA (1)	OA05515A (pl)
PL (1)	PL101143B1 (pl)
PT (1)	PT65970B (pl)
SE (1)	SE434396B (pl)
SU (1)	SU633476A3 (pl)
YU (1)	YU39980B (pl)
ZA (1)	ZA767112B (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2592879B1 (fr) *	1986-01-13	1988-04-29	Roussel Uclaf	Nouveaux derives de la decahydroquinoleine, leur procede de preparation, les intermediaires de preparation, leur application a titre de medicaments et les compositions les renfermant
PT1732933E (pt) *	2004-03-26	2008-10-20	Lilly Co Eli	Compostos para o tratamento da dislipidémia

1975
- 1975-12-16 GB GB51507/75A patent/GB1515540A/en not_active Expired
1976
- 1976-11-26 IE IE2613/76A patent/IE44355B1/en unknown
- 1976-11-29 NZ NZ182758A patent/NZ182758A/xx unknown
- 1976-11-29 ZA ZA00767112A patent/ZA767112B/xx unknown
- 1976-12-07 AU AU20328/76A patent/AU509897B2/en not_active Expired
- 1976-12-08 NL NL7613629A patent/NL7613629A/xx not_active Application Discontinuation
- 1976-12-13 CH CH1565976A patent/CH618970A5/fr not_active IP Right Cessation
- 1976-12-13 AR AR265813A patent/AR214988A1/es active
- 1976-12-13 CA CA267,706A patent/CA1077040A/en not_active Expired
- 1976-12-14 FR FR7637621A patent/FR2335224A1/fr active Granted
- 1976-12-14 MX MX765223A patent/MX5798E/es unknown
- 1976-12-15 HU HU76LA900A patent/HU175391B/hu unknown
- 1976-12-15 NO NO764251A patent/NO145916C/no unknown
- 1976-12-15 JP JP51151456A patent/JPS6022711B2/ja not_active Expired
- 1976-12-15 PT PT65970A patent/PT65970B/pt unknown
- 1976-12-15 OA OA56017A patent/OA05515A/xx unknown
- 1976-12-15 BE BE173281A patent/BE849431A/xx not_active IP Right Cessation
- 1976-12-15 SU SU762428755A patent/SU633476A3/ru active
- 1976-12-15 DE DE2656678A patent/DE2656678C2/de not_active Expired
- 1976-12-15 IT IT30441/76A patent/IT1065969B/it active
- 1976-12-15 SE SE7614105A patent/SE434396B/xx not_active IP Right Cessation
- 1976-12-15 DK DK564876A patent/DK564876A/da not_active Application Discontinuation
- 1976-12-15 FI FI763603A patent/FI63023C/fi not_active IP Right Cessation
- 1976-12-15 DD DD7600196381A patent/DD128709A5/xx unknown
- 1976-12-16 AT AT932076A patent/AT357535B/de not_active IP Right Cessation
- 1976-12-16 YU YU3071/76A patent/YU39980B/xx unknown
- 1976-12-16 PL PL1976194452A patent/PL101143B1/pl unknown
- 1976-12-16 ES ES454285A patent/ES454285A1/es not_active Expired

Also Published As

Publication number	Publication date
JPS52102284A (en)	1977-08-27
SE434396B (sv)	1984-07-23
FR2335224B1 (pl)	1980-03-14
SE7614105L (sv)	1977-06-17
NO145916C (no)	1982-06-23
DE2656678A1 (de)	1977-06-30
ZA767112B (en)	1978-07-26
AU509897B2 (en)	1980-05-29
DK564876A (da)	1977-06-17
OA05515A (fr)	1981-04-30
IE44355B1 (en)	1981-11-04
IE44355L (en)	1977-06-16
SU633476A3 (ru)	1978-11-15
CA1077040A (en)	1980-05-06
DD128709A5 (de)	1977-12-07
AU2032876A (en)	1978-06-15
PL101143B1 (pl)	1978-12-30
FI763603A (pl)	1977-06-17
PT65970B (fr)	1978-06-16
JPS6022711B2 (ja)	1985-06-03
GB1515540A (en)	1978-06-28
ES454285A1 (es)	1977-11-16
NO145916B (no)	1982-03-15
HU175391B (hu)	1980-07-28
FI63023C (fi)	1983-04-11
DE2656678C2 (de)	1986-12-04
NL7613629A (nl)	1977-06-20
FR2335224A1 (fr)	1977-07-15
YU39980B (en)	1985-06-30
PT65970A (fr)	1977-01-01
AT357535B (de)	1980-07-10
IT1065969B (it)	1985-03-04
FI63023B (fi)	1982-12-31
NO764251L (pl)	1977-06-17
MX5798E (es)	1984-07-25
BE849431A (fr)	1977-06-15
AR214988A1 (es)	1979-08-31
YU307176A (en)	1982-08-31
NZ182758A (en)	1979-03-28
ATA932076A (de)	1979-12-15

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EP0506539B1 (fr)	1997-05-02	Amides alkyl hétérocycliques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
FR2679903A1 (fr)	1993-02-05	Derives de la n-sulfonyl indoline portant une fonction amidique, leur preparation, les compositions pharmaceutiques en contenant.
EP0527687A2 (fr)	1993-02-17	Nouveaux dérivés d'aryléthylamines, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
EP0447285A1 (fr)	1991-09-18	Nouveaux dérivés à structure naphtalénique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
FR2487829A2 (fr)	1982-02-05	Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
CH637927A5 (fr)	1983-08-31	Derives de 4-amino-5-alkylsulfonyl ortho-anisamides et leurs procedes de preparation.
JPS6254095B2 (pl)	1987-11-13
FR2531707A1 (fr)	1984-02-17	Trifluoromethylphenyltetrahydropyridines substituees a activite anorexigene, un procede de preparation et compositions pharmaceutiques
EP0007824B1 (fr)	1981-07-22	Nouveaux dérivés de benzofuranne, leur procédé de préparation et composition thérapeutiqueles contenant.
EP0031753A1 (fr)	1981-07-08	Nouveaux dérivés de la (pipéridyl-4)-2 (quinolyl-4)-1 éthanone, produits intermédiaires et procédés pour leur préparation, et leur utilisation comme médicaments
EP0366511A1 (fr)	1990-05-02	Nouveaux dérivés benzoxazolinoniques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
EP0004494B1 (fr)	1982-02-17	Nouveaux dérivés de 1,3-dihydro 3-(1-(2-(2,3-dihydro 1,4-benzo-dioxin-2-yl)2-hydroxy éthyl)pipéridin-4-yl)2H-indol 2-one, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant
EP0024960A2 (fr)	1981-03-11	Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux
WO1991019714A1 (fr)	1991-12-26	Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0385848A1 (fr)	1990-09-05	Nouveaux dérivés benzoxazolinoniques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
CH618970A5 (en)	1980-08-29	Process for the preparation of 4-amido-trans-decahydroquinoline derivatives
CH659469A5 (fr)	1987-01-30	Derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation et les medicaments et compositions les renfermant.
EP0015171B1 (fr)	1982-04-28	Dérivés condensés de pyrrolidine ou de pipéridine, leur procédé de préparation et composition les contenant
FR2597865A1 (fr)	1987-10-30	Nouveaux derives d'un acide benzyl alkyl carboxylique substitue par un radical 4-pyridinyl aminocarbonyle, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant
CA2045849A1 (fr)	1991-12-30	Derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CH634311A5 (fr)	1983-01-31	Derives du benzo(d)thiazole, leur procede de preparation et leurs applications en therapeutique.
FR652M (fr)	1961-06-19	Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels.
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
CH674845A5 (pl)	1990-07-31
CA2015626A1 (fr)	1990-10-28	Derives benzothiazolinoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Legal Events

Date	Code	Title	Description
1981-11-13	PFA	Name/firm changed	Owner name: SANOFI
1981-11-13	PUE	Assignment	Owner name: OMNIUM FINANCIER AQUITAINE POUR L'HYGIENE ET LA SA
1988-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased