CH625521A5 - - Google Patents

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Info

Publication number: CH625521A5
Authority: CH; Switzerland
Prior art keywords: group; atoms; alkyl; hydrogen; formula
Prior art date: 1976-10-15

Application number

CH1308676A

Other languages

German (de)

English (en)

Inventor

Emil Dr Pfenninger

Original Assignee

Sandoz Ag

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

1976-10-15

Filing date

1976-10-15

Publication date

1981-09-30

1976-10-15 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-10-15 Priority to CH1308676A priority Critical patent/CH625521A5/de

1977-10-05 Priority to DE19772744772 priority patent/DE2744772A1/de

1977-10-06 Priority to FI772955A priority patent/FI61313C/fi

1977-10-06 Priority to SE7711185A priority patent/SE7711185L/xx

1977-10-06 Priority to DK443477A priority patent/DK143802C/da

1977-10-10 Priority to GB42063/77A priority patent/GB1589396A/en

1977-10-11 Priority to NL7711125A priority patent/NL7711125A/xx

1977-10-12 Priority to FR7730693A priority patent/FR2367765A1/fr

1977-10-13 Priority to BE181731A priority patent/BE859709A/xx

1977-10-13 Priority to IL53120A priority patent/IL53120A/xx

1977-10-13 Priority to IE2094/77A priority patent/IE46161B1/en

1977-10-13 Priority to PT67154A priority patent/PT67154B/pt

1977-10-13 Priority to AU29659/77A priority patent/AU514226B2/en

1977-10-13 Priority to NZ185419A priority patent/NZ185419A/xx

1977-10-14 Priority to JP12258577A priority patent/JPS5384994A/ja

1977-10-14 Priority to ZA00776138A priority patent/ZA776138B/xx

1977-10-14 Priority to AT0736777A priority patent/AT367421B/de

1977-10-14 Priority to CA288,714A priority patent/CA1104136A/en

1977-10-14 Priority to ES463228A priority patent/ES463228A1/es

1977-10-14 Priority to PH20332A priority patent/PH14888A/en

1979-04-06 Priority to US06/027,893 priority patent/US4235907A/en

1981-09-30 Publication of CH625521A5 publication Critical patent/CH625521A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
WUCIMUWUAXJBRW-UHFFFAOYSA-N c1ncc2[nH]c3ccccc3cc12 Chemical class c1ncc2[nH]c3ccccc3cc12 WUCIMUWUAXJBRW-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 23
150000002431 hydrogen Chemical class 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229960001340 histamine Drugs 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000243 solution Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
210000003630 histaminocyte Anatomy 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000427 antigen Substances 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
108091007433 antigens Proteins 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
210000003491 skin Anatomy 0.000 description 3
230000002269 spontaneous effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
208000034656 Contusions Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
206010070834 Sensitisation Diseases 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
-1 aromatic nitro compounds Chemical class 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
FVNFJCUAVCGCIA-UHFFFAOYSA-N ethyl 4-anilino-1-benzoyl-2,5-dihydropyrrole-3-carboxylate Chemical compound C1C(C(=O)OCC)=C(NC=2C=CC=CC=2)CN1C(=O)C1=CC=CC=C1 FVNFJCUAVCGCIA-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
230000008313 sensitization Effects 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
241000588832 Bordetella pertussis Species 0.000 description 1
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
235000001188 Peltandra virginica Nutrition 0.000 description 1
244000197580 Poria cocos Species 0.000 description 1
235000008599 Poria cocos Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000369 cadmium(II) sulfate Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
LFEOOBLUOBPNOE-UHFFFAOYSA-N formaldehyde;2-(4-methoxyphenyl)-n-methylethanamine Chemical compound O=C.CNCCC1=CC=C(OC)C=C1 LFEOOBLUOBPNOE-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229940066827 pertussis vaccine Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH1308676A 1976-10-15 1976-10-15 CH625521A5 (zh)

Priority Applications (21)

Application Number	Priority Date	Filing Date	Title
CH1308676A CH625521A5 (zh)	1976-10-15	1976-10-15
DE19772744772 DE2744772A1 (de)	1976-10-15	1977-10-05	Neue chinolinderivate, ihre herstellung und verwendung
FI772955A FI61313C (fi)	1976-10-15	1977-10-06	Analogifoerfarande foer framstaellning av nya pyrrolo(3,4-b)kinolin-9-on-derivat anvaendbara saosom laekemedel
SE7711185A SE7711185L (sv)	1976-10-15	1977-10-06	Nya organiska foreningar, deras framstellning och anvendning
DK443477A DK143802C (da)	1976-10-15	1977-10-06	Analogifremgangsmaade til fremstilling af pyrrolo(3,4-b)quinolin-9-on-derivater
GB42063/77A GB1589396A (en)	1976-10-15	1977-10-10	1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-one and derivatives thereof
NL7711125A NL7711125A (nl)	1976-10-15	1977-10-11	Werkwijzen voor het bereiden en toepassen van een aromatische verbinding.
FR7730693A FR2367765A1 (fr)	1976-10-15	1977-10-12	Nouvelles quinolones, leur preparation et leur application comme medicaments
BE181731A BE859709A (fr)	1976-10-15	1977-10-13	Nouvelles quinolones
IL53120A IL53120A (en)	1976-10-15	1977-10-13	1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-one derivatives,their production and pharmaceutical compositions containing them
IE2094/77A IE46161B1 (en)	1976-10-15	1977-10-13	1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-one and derivatives thereof
PT67154A PT67154B (en)	1976-10-15	1977-10-13	Process for preparing organic compounds with pharmaceutical activity
AU29659/77A AU514226B2 (en)	1976-10-15	1977-10-13	Pyrolo(3, 4-b) quinolin-9-one derivatives
NZ185419A NZ185419A (en)	1976-10-15	1977-10-13	1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-ones
JP12258577A JPS5384994A (en)	1976-10-15	1977-10-14	Improvement in organic compound
ZA00776138A ZA776138B (en)	1976-10-15	1977-10-14	Improvements in or relating to organic compounds
AT0736777A AT367421B (de)	1976-10-15	1977-10-14	Verfahren zur herstellung neuer 1,2,3,4-tetra-
CA288,714A CA1104136A (en)	1976-10-15	1977-10-14	¬1,2,3,4-tetrahydro-9h-pyrrolo¬3,4-b\|quinoline- 9-one derivatives\|
ES463228A ES463228A1 (es)	1976-10-15	1977-10-14	Procedimiento para preparar quinolinonas
PH20332A PH14888A (en)	1976-10-15	1977-10-14	1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-one derivative
US06/027,893 US4235907A (en)	1976-10-15	1979-04-06	Substituted-9H-pyrrolo[3,4-b]quinolin-9-ones and treatment of allergic conditions with them

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1308676A CH625521A5 (zh)	1976-10-15	1976-10-15

Publications (1)

Publication Number	Publication Date
CH625521A5 true CH625521A5 (zh)	1981-09-30

Family

ID=4389164

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1308676A CH625521A5 (zh)	1976-10-15	1976-10-15

Country Status (21)

Country	Link
US (1)	US4235907A (zh)
JP (1)	JPS5384994A (zh)
AT (1)	AT367421B (zh)
AU (1)	AU514226B2 (zh)
BE (1)	BE859709A (zh)
CA (1)	CA1104136A (zh)
CH (1)	CH625521A5 (zh)
DE (1)	DE2744772A1 (zh)
DK (1)	DK143802C (zh)
ES (1)	ES463228A1 (zh)
FI (1)	FI61313C (zh)
FR (1)	FR2367765A1 (zh)
GB (1)	GB1589396A (zh)
IE (1)	IE46161B1 (zh)
IL (1)	IL53120A (zh)
NL (1)	NL7711125A (zh)
NZ (1)	NZ185419A (zh)
PH (1)	PH14888A (zh)
PT (1)	PT67154B (zh)
SE (1)	SE7711185L (zh)
ZA (1)	ZA776138B (zh)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA72611C2 (uk) *	2000-05-17	2005-03-15	Орто-Макнейл Фармацевтикал, Інк.	Похідні заміщеного піролопіридинону, корисні як інгібітори фосфодіестерази
JP4484517B2 (ja)	2001-11-14	2010-06-16	オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド	ホスホジエステラーゼ阻害剤として有用な置換された四環式ピロロキノロン誘導体
DE60317684D1 (de) *	2002-06-19	2008-01-03	Janssen Pharmaceutica Nv	SUBSTITUIERTE 2,4-DIHYDROPYRROLOc3,4BÜCHINOLIN-9-ONDERIVATE, DIE SICH ALS PHOSPHODIESTERASEINHIBITOREN EIGNEN
CL2008003573A1 (es) *	2008-11-28	2011-02-18	Univ Talca	Metodo de sintesis enantioselectiva de intermediarios de beta-carbolina del tipo pirrolo-quinolonas por hidrogenacion con auxiliares quirales de cloroformiato.

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2023514A1 (de) *	1970-05-14	1971-12-02	Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von 5,6-gamma-Pyridonderivaten
DE2343549A1 (de) *	1973-08-29	1975-03-13	Thiemann Chem Pharm Fab	4-hydroxychinolinverbindungen und solche verbindungen enthaltende arzneimittel
DE2521544A1 (de)	1975-05-15	1976-12-02	Thomae Gmbh Dr K	Neue chinoline

1976
- 1976-10-15 CH CH1308676A patent/CH625521A5/de not_active IP Right Cessation
1977
- 1977-10-05 DE DE19772744772 patent/DE2744772A1/de not_active Withdrawn
- 1977-10-06 SE SE7711185A patent/SE7711185L/xx not_active Application Discontinuation
- 1977-10-06 FI FI772955A patent/FI61313C/fi not_active IP Right Cessation
- 1977-10-06 DK DK443477A patent/DK143802C/da not_active IP Right Cessation
- 1977-10-10 GB GB42063/77A patent/GB1589396A/en not_active Expired
- 1977-10-11 NL NL7711125A patent/NL7711125A/xx not_active Application Discontinuation
- 1977-10-12 FR FR7730693A patent/FR2367765A1/fr active Granted
- 1977-10-13 BE BE181731A patent/BE859709A/xx not_active IP Right Cessation
- 1977-10-13 PT PT67154A patent/PT67154B/pt unknown
- 1977-10-13 IE IE2094/77A patent/IE46161B1/en unknown
- 1977-10-13 NZ NZ185419A patent/NZ185419A/xx unknown
- 1977-10-13 IL IL53120A patent/IL53120A/xx unknown
- 1977-10-13 AU AU29659/77A patent/AU514226B2/en not_active Expired
- 1977-10-14 AT AT0736777A patent/AT367421B/de not_active IP Right Cessation
- 1977-10-14 CA CA288,714A patent/CA1104136A/en not_active Expired
- 1977-10-14 ES ES463228A patent/ES463228A1/es not_active Expired
- 1977-10-14 JP JP12258577A patent/JPS5384994A/ja active Pending
- 1977-10-14 PH PH20332A patent/PH14888A/en unknown
- 1977-10-14 ZA ZA00776138A patent/ZA776138B/xx unknown
1979
- 1979-04-06 US US06/027,893 patent/US4235907A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK443477A (da)	1978-04-16
PT67154B (en)	1979-06-07
PH14888A (en)	1982-01-08
IE46161B1 (en)	1983-03-09
FI61313C (fi)	1982-07-12
JPS5384994A (en)	1978-07-26
IL53120A (en)	1980-06-30
FI772955A (fi)	1978-04-16
DK143802B (da)	1981-10-12
BE859709A (fr)	1978-04-13
CA1104136A (en)	1981-06-30
AU514226B2 (en)	1981-01-29
ATA736777A (de)	1981-11-15
DK143802C (da)	1982-03-29
NZ185419A (en)	1980-08-26
IL53120A0 (en)	1977-12-30
US4235907A (en)	1980-11-25
IE46161L (en)	1978-04-15
SE7711185L (sv)	1978-04-16
AT367421B (de)	1982-07-12
ZA776138B (en)	1979-05-30
FR2367765B1 (zh)	1980-04-18
AU2965977A (en)	1979-04-26
NL7711125A (nl)	1978-04-18
ES463228A1 (es)	1979-01-01
DE2744772A1 (de)	1978-04-20
GB1589396A (en)	1981-05-13
FI61313B (fi)	1982-03-31
PT67154A (en)	1977-11-01
FR2367765A1 (fr)	1978-05-12

Publication	Publication Date	Title
DE2402398C3 (de)	1981-07-23	Aromatische Carbonsäureamid-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen
DE2822544C2 (zh)	1988-10-27
AT390257B (de)	1990-04-10	Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate
DE3033157A1 (de)	1982-04-01	7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
CH651827A5 (de)	1985-10-15	Carbostyrilderivate, verfahren zu ihrer herstellung und kardiotonische zusammensetzungen, welche diese enthalten.
DE2802493C2 (zh)	1989-01-26
CH439286A (de)	1967-07-15	Verfahren zur Herstellung neuer Piperidin-Verbindungen
DE2931418C2 (zh)	1989-06-29
DE2656468A1 (de)	1978-06-15	N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung
DE2449270C3 (de)	1980-07-10	2-[3-(4-Diphenylmethyl-piperarino)-propyl] -s-triazolo [13-a eckige Klammer zu pyridin, seine nicht toxischen Salze mit Säuren und ein Verfahren zu ihrer Herstellung
EP0080176B1 (de)	1986-02-19	Triazolochinazoline, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
CH625521A5 (zh)	1981-09-30
DE2816109A1 (de)	1978-10-26	Neue pyrrolochinoxaline, verfahren zu deren herstellung und pharmazeutische zusammensetzungen
DE2845857A1 (de)	1979-04-26	Benzo eckige klammer auf d eckige klammer zu thiazolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen
DE2322486C2 (de)	1982-06-03	as-Triazino [5,6-c] chinolin und seine Salze, Verfahren zur Herstellung derselben sowie diese Verbindungen enthaltende Arzneimittel
DE2900288A1 (de)	1979-07-12	Aminoderivate von pyrazol eckige klammer auf 1,5-a eckige klammer zu s-triazin, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE1695656B2 (de)	1974-06-06	l-Alkyl-4-aryl-2(lH)-chinazoIinone
DE2024049C3 (de)	1978-07-20	a-(3,4-Dihydroxyphenyl)-a- (2-piperidinyl)methanol
DE2448389A1 (de)	1975-04-17	Derivate von 4-hydroxy-3-nitro-alpha- pyridonen enthaltende arzneimittel, neue 4-hydroxy-3-nitro-alpha-pyridone und verfahren zu ihrer herstellung
DE2649855C2 (de)	1987-01-22	Substituierte 5-Acetyl-4-hydroxy-3-phenylamino-2H-pyran-2,6(3H)-dione, Verfahren zu deren Herstellung und deren Verwendung
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
CH647235A5 (de)	1985-01-15	4-(2,2-dialkylindan-1-yliden)piperidin derivate, ihre herstellung und verwendung.
DE2731039A1 (de)	1978-01-19	7-(substituierte)-7h-pyrrolo eckige klammer auf 3,2-f eckige klammer zu -chinazolin-1,3-diamine
DE1280878B (de)	1968-10-24	3-Aminoindazole
DE1200825B (de)	1965-09-16	Verfahren zur Herstellung von 3, 5-Dioxo-triazolidinen

Legal Events

Date	Code	Title	Description
1985-06-28	PL	Patent ceased
2024-10-31	PL	Patent ceased