DD202574A5 - Verfahren zur herstellung von 1,4,9,10-tetrahydro-pyrazolo (4,3-) pyrido (3,2-b) (1,4)- diazepin-10-onen - Google Patents

Verfahren zur herstellung von 1,4,9,10-tetrahydro-pyrazolo (4,3-) pyrido (3,2-b) (1,4)- diazepin-10-onen Download PDF

Info

Publication number: DD202574A5
Authority: DD; German Democratic Republic
Prior art keywords: tetrahydro; pyrazolo; general formula; preparation; dimethyl
Prior art date: 1981-06-06

Application number

DD82240437A

Other languages

German (de)

English (en)

Inventor

Schmidt

Engel

Eberlein

Trummlitz

Engelhardt

Original Assignee

Thomae Gmbh Dr K

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.)

1981-06-06

Filing date

1982-06-03

Publication date

1983-09-21

1982-06-03 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1983-09-21 Publication of DD202574A5 publication Critical patent/DD202574A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000001875 compounds Chemical class 0.000 abstract description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
229910052739 hydrogen Inorganic materials 0.000 abstract description 7
239000001257 hydrogen Substances 0.000 abstract description 7
230000001754 anti-pyretic effect Effects 0.000 abstract description 6
239000002260 anti-inflammatory agent Substances 0.000 abstract description 5
230000001741 anti-phlogistic effect Effects 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 5
230000000144 pharmacologic effect Effects 0.000 abstract description 5
230000000202 analgesic effect Effects 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
-1 2-chloro-3-pyridinyl Chemical group 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000012312 sodium hydride Substances 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
239000000243 solution Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000699666 Mus <mouse, genus> Species 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000011097 chromatography purification Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
206010065390 Inflammatory pain Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
208000000114 Pain Threshold Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
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238000003304 gavage Methods 0.000 description 3
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230000036407 pain Effects 0.000 description 3
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239000011541 reaction mixture Substances 0.000 description 3
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HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
ANGMMUPJSXUXGY-UHFFFAOYSA-N 1-methyl-4-nitro-1h-pyrazole-5-carboxylic acid Chemical compound CN1N=CC([N+]([O-])=O)=C1C(O)=O ANGMMUPJSXUXGY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 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
238000012417 linear regression Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000001665 trituration Methods 0.000 description 2
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
JREJQAWGQCMSIY-UHFFFAOYSA-N 1-methyl-pyrazole-5-carboxylic acid Chemical compound CN1N=CC=C1C(O)=O JREJQAWGQCMSIY-UHFFFAOYSA-N 0.000 description 1
MCTUAJONAXPWLC-UHFFFAOYSA-N 2,5-dimethyl-4-nitropyrazole-3-carboxylic acid Chemical compound CC1=NN(C)C(C(O)=O)=C1[N+]([O-])=O MCTUAJONAXPWLC-UHFFFAOYSA-N 0.000 description 1
XISBGHUTERBJEN-UHFFFAOYSA-N 2-aminopyrazole-3-carboxamide Chemical compound NC(=O)C1=CC=NN1N XISBGHUTERBJEN-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
YXCXJDABMFQKRK-UHFFFAOYSA-N 4-amino-n-(2-chloropyridin-3-yl)-2,5-dimethylpyrazole-3-carboxamide Chemical compound CC1=NN(C)C(C(=O)NC=2C(=NC=CC=2)Cl)=C1N YXCXJDABMFQKRK-UHFFFAOYSA-N 0.000 description 1
ZUSTWVKIIVVIIW-UHFFFAOYSA-N 4-amino-n-(2-chloropyridin-3-yl)-2-methylpyrazole-3-carboxamide Chemical compound CN1N=CC(N)=C1C(=O)NC1=CC=CN=C1Cl ZUSTWVKIIVVIIW-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
ZMAXXOYJWZZQBK-UHFFFAOYSA-N 5334-40-7 Chemical compound OC(=O)C1=NNC=C1[N+]([O-])=O ZMAXXOYJWZZQBK-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960001301 amobarbital Drugs 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007123 defense Effects 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
JOUBJJWSMWRSCQ-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-2-methyl-4-nitropyrazole-3-carboxamide Chemical compound CN1N=CC([N+]([O-])=O)=C1C(=O)NC1=CC=CN=C1Cl JOUBJJWSMWRSCQ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005303 weighing Methods 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/16—Halogen atoms or nitro radicals

Landscapes

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

DD82240437A 1981-06-06 1982-06-03 Verfahren zur herstellung von 1,4,9,10-tetrahydro-pyrazolo (4,3-) pyrido (3,2-b) (1,4)- diazepin-10-onen DD202574A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813122670 DE3122670A1 (de)	1981-06-06	1981-06-06	"neue 1,4,9,10-tetrahydro-pyrazolo(4,3-e) pyrido(3,2-b)(1,4)diazepin-10-one, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von pharmazeutischen wirkstoffen"

Publications (1)

Publication Number	Publication Date
DD202574A5 true DD202574A5 (de)	1983-09-21

Family

ID=6134176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82240437A DD202574A5 (de)	1981-06-06	1982-06-03	Verfahren zur herstellung von 1,4,9,10-tetrahydro-pyrazolo (4,3-) pyrido (3,2-b) (1,4)- diazepin-10-onen

Country Status (27)

Country	Link
US (1)	US4381303A (cs)
EP (1)	EP0066774B1 (cs)
JP (1)	JPS57212182A (cs)
KR (1)	KR880001719B1 (cs)
AR (1)	AR229124A1 (cs)
AT (1)	ATE10744T1 (cs)
AU (1)	AU552765B2 (cs)
CA (1)	CA1167440A (cs)
CS (1)	CS226743B2 (cs)
DD (1)	DD202574A5 (cs)
DE (2)	DE3122670A1 (cs)
DK (1)	DK253382A (cs)
ES (1)	ES512846A0 (cs)
FI (1)	FI71560C (cs)
GB (1)	GB2117755B (cs)
GR (1)	GR76438B (cs)
HU (1)	HU186067B (cs)
IE (1)	IE53067B1 (cs)
IL (1)	IL65977A (cs)
NO (1)	NO158063C (cs)
NZ (1)	NZ200859A (cs)
PH (1)	PH17719A (cs)
PL (1)	PL135845B1 (cs)
PT (1)	PT75016B (cs)
SU (1)	SU1103795A3 (cs)
YU (1)	YU118282A (cs)
ZA (1)	ZA823919B (cs)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3643666A1 (de) *	1986-12-20	1988-06-30	Thomae Gmbh Dr K	Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4749788A (en) *	1987-04-13	1988-06-07	A. H. Robins Company, Incorporated	Process for the preparation of aryl-pyrido(1,4) benzodiazepines
US5366972A (en) *	1989-04-20	1994-11-22	Boehringer Ingelheim Pharmaceuticals, Inc.	5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection
DK0410148T3 (da) *	1989-06-28	1994-08-08	Boehringer Ingelheim Pharma	Hidtil ukendte 5,11-dihydro-6H-dipyrido(3,2-b:2,3-e)-(1,4)diazepin-6-oner og -thioner og deres anvendelse til forebyggelse eller behandling af AIDS
CA2052946A1 (en) *	1990-10-19	1992-04-20	Karl G. Grozinger	Method for the preparation of 5,11-dihydro-6h-dipyrido ¬3,2-b:2', 3'-e\| ¬1,4\|diazepines
ATE177099T1 (de) *	1993-12-29	1999-03-15	Pfizer	Diazabicyclische neurokinin antagonisten
CA2183571A1 (en) *	1994-02-18	1995-08-24	Karl D. Hargrave	2-heteroaryl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepines and their use in the prevention or treatment of hiv infection
ES2137113B1 (es)	1997-07-29	2000-09-16	Almirall Prodesfarma Sa	Nuevos derivados de triazolo-piridazinas heterociclicos.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3450694A (en) *	1966-02-23	1969-06-17	Abbott Lab	Substituted benzoxazepines and benzothiazepines
DE2707269A1 (de) *	1977-02-19	1978-08-24	Hoechst Ag	Heterocyclische stickstoffverbindungen und verfahren zu ihrer herstellung
CA1154762A (en) *	1979-08-03	1983-10-04	Georg Rainer	Substituted tetraazatricyclic compounds, a process for their preparation, their use and medicaments containing them

1981
- 1981-06-06 DE DE19813122670 patent/DE3122670A1/de not_active Withdrawn
1982
- 1982-05-13 US US06/377,911 patent/US4381303A/en not_active Expired - Fee Related
- 1982-05-25 SU SU823441915A patent/SU1103795A3/ru active
- 1982-05-25 AT AT82104549T patent/ATE10744T1/de not_active IP Right Cessation
- 1982-05-25 DE DE8282104549T patent/DE3261530D1/de not_active Expired
- 1982-05-25 EP EP82104549A patent/EP0066774B1/de not_active Expired
- 1982-06-01 AR AR289564A patent/AR229124A1/es active
- 1982-06-02 GR GR68322A patent/GR76438B/el unknown
- 1982-06-03 YU YU01182/82A patent/YU118282A/xx unknown
- 1982-06-03 CS CS824137A patent/CS226743B2/cs unknown
- 1982-06-03 PL PL1982236742A patent/PL135845B1/pl unknown
- 1982-06-03 DD DD82240437A patent/DD202574A5/de unknown
- 1982-06-03 KR KR8202494A patent/KR880001719B1/ko not_active Expired
- 1982-06-04 IE IE1350/82A patent/IE53067B1/en unknown
- 1982-06-04 PT PT75016A patent/PT75016B/pt unknown
- 1982-06-04 IL IL65977A patent/IL65977A/xx unknown
- 1982-06-04 CA CA000404541A patent/CA1167440A/en not_active Expired
- 1982-06-04 JP JP57096080A patent/JPS57212182A/ja active Pending
- 1982-06-04 ZA ZA823919A patent/ZA823919B/xx unknown
- 1982-06-04 NO NO821882A patent/NO158063C/no unknown
- 1982-06-04 GB GB08216381A patent/GB2117755B/en not_active Expired
- 1982-06-04 HU HU821823A patent/HU186067B/hu unknown
- 1982-06-04 PH PH27402A patent/PH17719A/en unknown
- 1982-06-04 FI FI821992A patent/FI71560C/fi not_active IP Right Cessation
- 1982-06-04 NZ NZ200859A patent/NZ200859A/en unknown
- 1982-06-04 AU AU84605/82A patent/AU552765B2/en not_active Ceased
- 1982-06-04 ES ES512846A patent/ES512846A0/es active Granted
- 1982-06-04 DK DK253382A patent/DK253382A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU8460582A (en)	1982-12-16
GB2117755A (en)	1983-10-19
FI821992A0 (fi)	1982-06-04
IE53067B1 (en)	1988-05-25
PT75016B (de)	1985-05-17
NO158063C (no)	1988-07-06
CA1167440A (en)	1984-05-15
DK253382A (da)	1982-12-07
ES8304571A1 (es)	1983-03-01
DE3261530D1 (en)	1985-01-24
KR880001719B1 (ko)	1988-09-08
JPS57212182A (en)	1982-12-27
ATE10744T1 (de)	1984-12-15
KR840000543A (ko)	1984-02-25
NZ200859A (en)	1985-08-16
CS226743B2 (en)	1984-04-16
HU186067B (en)	1985-05-28
FI71560C (fi)	1987-01-19
NO158063B (no)	1988-03-28
IL65977A0 (en)	1982-09-30
IE821350L (en)	1982-12-06
GB2117755B (en)	1985-01-30
EP0066774B1 (de)	1984-12-12
US4381303A (en)	1983-04-26
YU118282A (en)	1986-04-30
ES512846A0 (es)	1983-03-01
PT75016A (de)	1982-07-01
SU1103795A3 (ru)	1984-07-15
GR76438B (cs)	1984-08-10
DE3122670A1 (de)	1982-12-23
ZA823919B (en)	1984-02-29
FI71560B (fi)	1986-10-10
AU552765B2 (en)	1986-06-19
PL135845B1 (en)	1985-12-31
PH17719A (en)	1984-11-21
NO821882L (no)	1982-12-07
IL65977A (en)	1984-12-31
PL236742A1 (en)	1984-03-26
AR229124A1 (es)	1983-06-15
EP0066774A1 (de)	1982-12-15

Publication	Publication Date	Title
EP0004279B1 (de)	1982-12-29	Verfahren zur Herstellung von 4-Pyridon-3-carbonsäuren, 1-Cyclopropyl-4-Pyridon-3-Carbonsäurederivate und diese enthaltende Arzneimittel
CH635823A5 (de)	1983-04-29	Verfahren zur herstellung von neuen 1-amidin-3-substituierten-phenylharnstoffen.
EP0022078B1 (de)	1984-07-25	Pyrazolochinoline, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate enthaltend diese Verbindungen
DE2336130A1 (de)	1974-01-31	Tricyclische verbindungen
DE68906200T2 (de)	1993-08-05	Kondensierte pyrazol-3-oxo-propannitril-derivate und verfahren zu deren herstellung.
EP0023707B1 (de)	1986-04-30	Substituierte Tetraazatricyclen, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende Arzneimittel
DE2234651A1 (de)	1974-04-04	Eckige klammer auf 1-(p-chlorbenzoyl)5-methoxy-2-methyl-3-indol eckige klammer zu acetoxyessigsaeure, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
EP0066774B1 (de)	1984-12-12	Neue 1,4,9,10-Tetrahydro-pyrazolo(4,3-e)pyrido(3,2-b)(1,4)-diazepin-10-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2424811A1 (de)	1975-12-18	Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
EP0072960B1 (de)	1989-06-07	1,5-Diphenylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2918778A1 (de)	1980-11-20	6-substituierte 11-alkylen-morphantridine
DE2740836A1 (de)	1979-03-22	Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE2633992C2 (cs)	1988-04-28
DE2548968A1 (de)	1977-05-12	Neue amino-benzoesaeureamide
DE2856908A1 (de)	1980-07-17	Neue chinoloncarbonsaeure-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische praeparate
DE2644121A1 (de)	1978-04-06	Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE2259471C2 (de)	1982-08-19	2-Halogen-9-phenyl-5,6-dihydro-7H-pyrido [2,3-f] [1,4] diazepinderivate
EP0113911B1 (de)	1986-03-26	Pyrido-triazolochinazoline, ihre Herstellung und Verwendung
CH641800A5 (de)	1984-03-15	Pyrido-pyrimidine, verfahren zu ihrer herstellung und die diese verbindungen enthaltenden arzneimittel.
EP0266711A1 (de)	1988-05-11	Neue 2,6-Diamono-3-halogenobenzyl-pyridine und Verfahren zu ihrer Herstellung sowie ihre Verwendung in Pharmazeutika
DE2423642C2 (de)	1986-11-20	Substituierte 6,7,8,9-Tetrahydro-1H-pyrazolo[3,4-b][1,5]-diazocinverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE3121137A1 (de)	1982-12-16	Neue pyridazino(4,5-b)indole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und deren herstellung"
DE2525024A1 (de)	1976-12-30	1,5-diphenylpyrazole und diese enthaltende arzneimittel
AT355581B (de)	1980-03-10	Verfahren zur herstellung neuer pyrido- benzodiazepinone und ihrer salze
DE2308732A1 (de)	1973-09-06	Neue 4,6-dioxo-pyridochinolin-2,8-dicarbonsaeure-derivate