CA1234112A - Pyrimido(4,5-g)quinolines et produits intermediaires - Google Patents

Pyrimido(4,5-g)quinolines et produits intermediaires

Info

Publication number: CA1234112A
Authority: CA; Canada
Prior art keywords: trans; propyl; quinoline; formula; octahydropyrimido
Prior art date: 1984-06-08
Legal status (The legal status 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 status listed.): Expired

Application number

CA000456153A

Other languages

English (en)

Inventor

Mark M. Foreman

Diane L. Huser

John M. Schaus

David T. Wong

Richard N. Booher

Edmund C. Kornfeld

Cynthia L. Nichols

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1984-06-08

Filing date

1984-06-08

Publication date

1988-03-15

1984-06-08 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1984-06-08 Priority to CA000456153A priority Critical patent/CA1234112A/fr

1988-03-15 Application granted granted Critical

1988-03-15 Publication of CA1234112A publication Critical patent/CA1234112A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 10
BEMDDSUTPVYURP-UHFFFAOYSA-N pyrido[2,3-g]quinazoline Chemical class C1=NC=NC2=CC3=CC=CN=C3C=C21 BEMDDSUTPVYURP-UHFFFAOYSA-N 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 52
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 7
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 121
150000001875 compounds Chemical class 0.000 claims description 83
238000000034 method Methods 0.000 claims description 43
239000002253 acid Substances 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
-1 ketone compound Chemical class 0.000 claims description 15
230000008569 process Effects 0.000 claims description 15
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 claims description 11
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 claims description 4
BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 claims description 4
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
NQQVLNFSVPLPII-UHFFFAOYSA-N 1,1-dimethylguanidine;hydrochloride Chemical compound [Cl-].CN(C)C([NH3+])=N NQQVLNFSVPLPII-UHFFFAOYSA-N 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
MIYGGZBSUPJUSX-TZMCWYRMSA-N (4ar,8ar)-7-(dimethylaminomethylidene)-1-propyl-3,4,4a,5,8,8a-hexahydro-2h-quinolin-6-one Chemical compound C1C(=O)C(=CN(C)C)C[C@H]2N(CCC)CCC[C@@H]21 MIYGGZBSUPJUSX-TZMCWYRMSA-N 0.000 claims 1
UEKDYDQPOFVKAZ-KWQFWETISA-N (5as,9as)-6-methyl-5a,7,8,9,9a,10-hexahydro-5h-pyrido[2,3-g]quinazolin-2-amine Chemical compound NC1=NC=C2C[C@@H]3N(C)CCC[C@H]3CC2=N1 UEKDYDQPOFVKAZ-KWQFWETISA-N 0.000 claims 1
TUFADSGTJUOBEH-GWCFXTLKSA-N (5as,9as)-6-propyl-5a,7,8,9,9a,10-hexahydro-5h-pyrido[2,3-g]quinazolin-2-amine Chemical compound NC1=NC=C2C[C@@H]3N(CCC)CCC[C@H]3CC2=N1 TUFADSGTJUOBEH-GWCFXTLKSA-N 0.000 claims 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
AFHDOPKXKWUMQE-ZYHUDNBSSA-N CN1CCC[C@@H]2CC(C(C[C@@H]12)=CN(C)C)=O Chemical compound CN1CCC[C@@H]2CC(C(C[C@@H]12)=CN(C)C)=O AFHDOPKXKWUMQE-ZYHUDNBSSA-N 0.000 claims 1
150000002576 ketones Chemical class 0.000 abstract description 12
108010057464 Prolactin Proteins 0.000 abstract description 9
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230000015572 biosynthetic process Effects 0.000 abstract description 9
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ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 6
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract description 5
206010020772 Hypertension Diseases 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
229940111121 antirheumatic drug quinolines Drugs 0.000 abstract description 3
150000003248 quinolines Chemical class 0.000 abstract description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
239000011541 reaction mixture Substances 0.000 description 41
239000000243 solution Substances 0.000 description 35
239000003814 drug Substances 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
229940079593 drug Drugs 0.000 description 29
241000700159 Rattus Species 0.000 description 27
239000000556 agonist Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 24
238000002360 preparation method Methods 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
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238000004458 analytical method Methods 0.000 description 17
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000012458 free base Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 14
229940095074 cyclic amp Drugs 0.000 description 14
239000003981 vehicle Substances 0.000 description 14
229960003638 dopamine Drugs 0.000 description 12
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000000284 extract Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
229960000443 hydrochloric acid Drugs 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000001793 charged compounds Chemical class 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
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239000007858 starting material Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 6
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230000008020 evaporation Effects 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
230000003287 optical effect Effects 0.000 description 6
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239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
208000007623 Lordosis Diseases 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000004872 arterial blood pressure Effects 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
230000000747 cardiac effect Effects 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
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239000000843 powder Substances 0.000 description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 3
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DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
239000013641 positive control Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
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239000008213 purified water Substances 0.000 description 1
NYWQXKOAQGNXBO-UHFFFAOYSA-N quinoline;dihydrobromide Chemical compound Br.Br.N1=CC=CC2=CC=CC=C21 NYWQXKOAQGNXBO-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
229940124550 renal vasodilator Drugs 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
CXYRUNPLKGGUJF-RAFJPFSSSA-M scopolamine methobromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-RAFJPFSSSA-M 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
230000035936 sexual power Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000003319 supportive effect Effects 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000456153A 1984-06-08 1984-06-08 Pyrimido(4,5-g)quinolines et produits intermediaires Expired CA1234112A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000456153A CA1234112A (fr)	1984-06-08	1984-06-08	Pyrimido(4,5-g)quinolines et produits intermediaires

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000456153A CA1234112A (fr)	1984-06-08	1984-06-08	Pyrimido(4,5-g)quinolines et produits intermediaires

Publications (1)

Publication Number	Publication Date
CA1234112A true CA1234112A (fr)	1988-03-15

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ID=4128058

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Application Number	Title	Priority Date	Filing Date
CA000456153A Expired CA1234112A (fr)	1984-06-08	1984-06-08	Pyrimido(4,5-g)quinolines et produits intermediaires

Country Status (1)

Country	Link
CA (1)	CA1234112A (fr)

1984
- 1984-06-08 CA CA000456153A patent/CA1234112A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-03-15	MKEX	Expiry

Publication	Publication Date	Title
US4501890A (en)	1985-02-26	Trans-(±)-2,4,6-substituted-5,5a,6,7,8,9,9a,10-octahydro-pyrimido[4,5-g]quinolines
JPH0528236B2 (fr)	1993-04-23
EP0145121B1 (fr)	1991-08-14	Pyrazoloquinoléines, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4537893A (en)	1985-08-27	Octahydrothiazolo[4,5-g]quinolines and use as prolactin secretion inhibitors
US4659832A (en)	1987-04-21	Process for the preparation of octahydro-oxazolo [4,5-G]quinolines
EP0139393B1 (fr)	1991-05-15	Pyrimido(4,5-g)quinolines, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0207696A1 (fr)	1987-01-07	Dialkylaminotétrahydrobenzothiazoles et -oxazoles
CA1234112A (fr)	1988-03-15	Pyrimido(4,5-g)quinolines et produits intermediaires
EP0172697B1 (fr)	1991-09-25	Octahydro-oxazolo[4,5-g]quinoléines
EP0260642A2 (fr)	1988-03-23	Dérivés d'hexahydroquinoline condensés en [f] avec thiazolo comme agents dopaminergiques
EP4551212A2 (fr)	2025-05-14	Tryptamines et méthodes de traitement de troubles de l'humeur
NZ205030A (en)	1986-03-14	Optically pure isomers of trans-1-n-propyl-6oxodecahydroquinoline
US4599339A (en)	1986-07-08	Use of pyrimido[4,5-g]quinolines in treating parkinsonism
US4778894A (en)	1988-10-18	6 oxo-decahydroquinolines
US4596871A (en)	1986-06-24	Pyrazole-ring alkylated pyrazoloquinolines
KR880001454B1 (ko)	1988-08-10	피리미도[4,5-g]퀴놀린 유도체
CA1254203A (fr)	1989-05-16	Dialcoylaminotetrahydroquinazoline
US4698347A (en)	1987-10-06	Octahydro-oxazolo[4,5-g]quinolines derivatives and decahydro quinoline intermediates and their use as dopamine D-2 agonists
JPS6333383A (ja)	1988-02-13	新規テトラヒドロベンゾチアゾ−ル−キノリン類、その製法及び用途
US4587336A (en)	1986-05-06	Partially hydrogenated intermediate pyrazolo, pyrimido and thiazolo[1,4]benzoxazines
CA1292989C (fr)	1991-12-10	Pyridines hetero [f] carbocycliques en tant qu'agents dopaminergiques
HU199462B (en)	1990-02-28	Process for producing pyrimido/4,5-a/quinoline derivatives and pharmaceutical compositions comprising same
JPS63165382A (ja)	1988-07-08	ヘテロ〔ｆ〕縮合炭素環式ピリジン類