NO871879L - Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser. - Google Patents

Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser.

Info

Publication number: NO871879L
Authority: NO; Norway
Prior art keywords: pyrazol; formula; phenyl; alkyl; compound
Prior art date: 1986-05-07

Application number

NO871879A

Other languages

English (en)

Norwegian (no)

Other versions

NO871879D0 (no

Inventor

Richard Anthony Appleton

Sidney Clifford Burford

John Dixon

Original Assignee

Fisons Plc

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.)

1986-05-07

Filing date

1987-05-06

Publication date

1987-11-09

1986-05-07 Priority claimed from GB868611102A external-priority patent/GB8611102D0/en

1986-12-24 Priority claimed from GB868630906A external-priority patent/GB8630906D0/en

1987-05-06 Application filed by Fisons Plc filed Critical Fisons Plc

1987-05-06 Publication of NO871879D0 publication Critical patent/NO871879D0/no

1987-11-09 Publication of NO871879L publication Critical patent/NO871879L/no

Links

238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 12
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000001589 carboacyl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
238000005899 aromatization reaction Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
YLOCHNXWGDQLIH-UHFFFAOYSA-N 2-(1h-pyrazol-5-ylamino)phenol Chemical compound OC1=CC=CC=C1NC1=NNC=C1 YLOCHNXWGDQLIH-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
ZTBQVCJFZOKYJV-UHFFFAOYSA-N 1-benzyl-5-methyl-n-phenylpyrazol-3-amine Chemical compound N=1N(CC=2C=CC=CC=2)C(C)=CC=1NC1=CC=CC=C1 ZTBQVCJFZOKYJV-UHFFFAOYSA-N 0.000 claims description 2
XITDNKSONMUDPZ-UHFFFAOYSA-N 1-benzyl-n-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(CC=2C=CC=CC=2)C=C1 XITDNKSONMUDPZ-UHFFFAOYSA-N 0.000 claims description 2
YNLDOCYALPXWOV-UHFFFAOYSA-N 2-[(1-methylpyrazol-3-yl)amino]phenol Chemical compound CN1C=CC(NC=2C(=CC=CC=2)O)=N1 YNLDOCYALPXWOV-UHFFFAOYSA-N 0.000 claims description 2
QGBMZPFZRRUQGV-UHFFFAOYSA-N 4-(1h-pyrazol-5-ylamino)phenol Chemical compound C1=CC(O)=CC=C1NC1=NNC=C1 QGBMZPFZRRUQGV-UHFFFAOYSA-N 0.000 claims description 2
FGPOTFQRHSVAPE-UHFFFAOYSA-N 4-[(1-benzylpyrazol-3-yl)amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NN(CC=2C=CC=CC=2)C=C1 FGPOTFQRHSVAPE-UHFFFAOYSA-N 0.000 claims description 2
ANDSTFHJMKJIKO-UHFFFAOYSA-N 4-[(1-methylpyrazol-3-yl)amino]phenol Chemical compound CN1C=CC(NC=2C=CC(O)=CC=2)=N1 ANDSTFHJMKJIKO-UHFFFAOYSA-N 0.000 claims description 2
NKRXUTNZNMPPTN-UHFFFAOYSA-N 4-[(5-phenyl-1h-pyrazol-3-yl)amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NNC(C=2C=CC=CC=2)=C1 NKRXUTNZNMPPTN-UHFFFAOYSA-N 0.000 claims description 2
CPVDCIXTOJGKCD-UHFFFAOYSA-N 4-[3-(4-methoxyanilino)-1H-pyrazol-5-yl]phenol Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C=2C=CC(O)=CC=2)=C1 CPVDCIXTOJGKCD-UHFFFAOYSA-N 0.000 claims description 2
SGHPAUUSPSGRQB-UHFFFAOYSA-N 4-[[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1CN1N=C(NC=2C=CC(O)=CC=2)C=C1 SGHPAUUSPSGRQB-UHFFFAOYSA-N 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
AFMSYOHKVDOEFY-UHFFFAOYSA-N 5-methyl-n-phenyl-1h-pyrazol-3-amine Chemical compound N1C(C)=CC(NC=2C=CC=CC=2)=N1 AFMSYOHKVDOEFY-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
DZODIUGJYAUAEH-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-methyl-5-phenylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C)C(C=2C=CC=CC=2)=C1 DZODIUGJYAUAEH-UHFFFAOYSA-N 0.000 claims description 2
PVWSVMVCDCGOLW-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C)C=C1 PVWSVMVCDCGOLW-UHFFFAOYSA-N 0.000 claims description 2
SBBYLGZCLMFIJA-UHFFFAOYSA-N n-(4-methoxyphenyl)-1h-pyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC=C1 SBBYLGZCLMFIJA-UHFFFAOYSA-N 0.000 claims description 2
XYJWVEMIGXHRAA-UHFFFAOYSA-N n-(4-methoxyphenyl)-4,5-diphenyl-1h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XYJWVEMIGXHRAA-UHFFFAOYSA-N 0.000 claims description 2
UEGANPRZIFWNMJ-UHFFFAOYSA-N 1-[3-(4-methoxyanilino)pyrazol-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(C)=O)C=C1 UEGANPRZIFWNMJ-UHFFFAOYSA-N 0.000 claims 1
BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical compound ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
-1 methoxy, acetoxy Chemical group 0.000 description 6
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239000011541 reaction mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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239000002585 base Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
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NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
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230000000144 pharmacologic effect Effects 0.000 description 3
210000000813 small intestine Anatomy 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000011282 treatment Methods 0.000 description 3
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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235000011054 acetic acid Nutrition 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
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239000002260 anti-inflammatory agent Substances 0.000 description 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
HIYAVKIYRIFSCZ-UHFFFAOYSA-N calcium ionophore A23187 Natural products N=1C2=C(C(O)=O)C(NC)=CC=C2OC=1CC(C(CC1)C)OC1(C(CC1C)C)OC1C(C)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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239000013078 crystal Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
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210000003238 esophagus Anatomy 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000013265 extended release Methods 0.000 description 1
208000022195 farmer lung disease Diseases 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
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239000001530 fumaric acid Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
208000009326 ileitis Diseases 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
210000001589 microsome Anatomy 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
DAIALAXTILYAHE-UHFFFAOYSA-N n-(2-methoxyphenyl)-1-methylpyrazol-3-amine Chemical compound COC1=CC=CC=C1NC1=NN(C)C=C1 DAIALAXTILYAHE-UHFFFAOYSA-N 0.000 description 1
IIMMPVUXXYHFFW-UHFFFAOYSA-N n-(2-methoxyphenyl)-1h-pyrazol-5-amine Chemical compound COC1=CC=CC=C1NC1=CC=NN1 IIMMPVUXXYHFFW-UHFFFAOYSA-N 0.000 description 1
HVAMZIRCNOJSMJ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-phenylprop-2-ynethioamide Chemical compound C1=CC(OC)=CC=C1NC(=S)C#CC1=CC=CC=C1 HVAMZIRCNOJSMJ-UHFFFAOYSA-N 0.000 description 1
XNKUXEFTNCRWAX-UHFFFAOYSA-N n-(4-methoxyphenyl)-5-methyl-1h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C)=C1 XNKUXEFTNCRWAX-UHFFFAOYSA-N 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
210000003024 peritoneal macrophage Anatomy 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent 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
238000011321 prophylaxis Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011002 quantification Methods 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- C07D231/38—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO871879A 1986-05-07 1987-05-06 Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser. NO871879L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB868611102A GB8611102D0 (en)	1986-05-07	1986-05-07	Heterocyclic compounds
GB868630906A GB8630906D0 (en)	1986-12-24	1986-12-24	Heterocyclic compounds

Publications (2)

Publication Number	Publication Date
NO871879D0 NO871879D0 (no)	1987-05-06
NO871879L true NO871879L (no)	1987-11-09

Family

ID=26290729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO871879A NO871879L (no)	1986-05-07	1987-05-06	Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser.

Country Status (13)

Country	Link
US (1)	US4803216A (xx)
EP (1)	EP0248523B1 (xx)
KR (1)	KR870011101A (xx)
AT (1)	AT390732B (xx)
AU (1)	AU595602B2 (xx)
CA (1)	CA1305157C (xx)
DE (1)	DE3773746D1 (xx)
DK (1)	DK231687A (xx)
FI (1)	FI871974L (xx)
IL (1)	IL82421A0 (xx)
NO (1)	NO871879L (xx)
NZ (1)	NZ220214A (xx)
PT (1)	PT84831B (xx)

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GR900100380A (el) *	1989-05-20	1991-10-10	Fisons Plc	Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης.
DE4234886A1 (de) *	1992-10-16	1994-04-21	Wella Ag	Neue N-Phenylaminopyrazol-Derivate sowie Mittel und Verfahren zur Färbung von Haaren
GB9312853D0 (en) *	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5500439A (en) *	1993-12-09	1996-03-19	Alteon Inc.	Aminopyrazoles
US5922751A (en) *	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US5591776A (en) *	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
WO1996000218A1 (en) *	1994-06-24	1996-01-04	Euro-Celtique, S.A.	Compounds for and method of inhibiting phosphodiesterase iv
ATE247655T1 (de) *	1994-12-13	2003-09-15	Euro Celtique Sa	Dreifachsubstituierte thioxanthine
EP0814809B1 (en) *	1994-12-13	2003-08-13	Euroceltique S.A.	Aryl thioxanthines
US6025361A (en) *	1994-12-13	2000-02-15	Euro-Celtique, S.A.	Trisubstituted thioxanthines
US6166041A (en) *	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6075016A (en) *	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US5864037A (en) *	1996-06-06	1999-01-26	Euro-Celtique, S.A.	Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
US5744473A (en) *	1996-09-16	1998-04-28	Euro-Celtique, S.A.	PDE IV inhibitors: "bis-compounds"
EP1554572B1 (en)	2001-07-25	2009-10-14	Raptor Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
WO2004076414A2 (en) *	2003-02-27	2004-09-10	Smithkline Beecham Corporation	Novel compounds
GB0326601D0 (en) *	2003-11-14	2003-12-17	Novartis Ag	Organic compounds
CN101287411B (zh)	2005-04-28	2013-03-06	普罗秋斯生物医学公司	药物信息系统及其用途
JO3019B1 (ar)	2006-04-19	2016-09-05	Janssen Pharmaceutica Nv	ثلاثي مستبدل 4،2،1-ثلاثي زولات
EP2063905B1 (en)	2006-09-18	2014-07-30	Raptor Pharmaceutical Inc	Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates
CN101827836B (zh)	2007-10-18	2014-02-19	詹森药业有限公司	三取代的1,2,4-三唑化合物
JO2784B1 (en)	2007-10-18	2014-03-15	شركة جانسين فارماسوتيكا ان. في	5,3,1 - Triazole substitute derivative
EP2257535B1 (en)	2008-03-19	2013-11-06	Janssen Pharmaceutica N.V.	Trisubstituted 1,2,4-triazoles as nicotinic acetylcholine receptor modulators
TWI440634B (zh) *	2008-05-09	2014-06-11	Janssen Pharmaceutica Nv	經三取代之吡唑類
HUE059078T2 (hu)	2009-02-20	2022-10-28	Enhanx Biopharm Inc	Glutation-alapú hatóanyagszállító rendszer
KR101909711B1 (ko)	2009-05-06	2018-12-19	라보라토리 스킨 케어, 인크.	활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법
CN102574832B (zh)	2009-09-17	2014-09-24	詹森药业有限公司	取代的n-苯基-1-(4-吡啶基)-1h-吡唑-3-胺
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates
US9828351B2 (en) *	2014-06-26	2017-11-28	Monash University	Enzyme interacting agents
WO2019156439A1 (en)	2018-02-07	2019-08-15	Korea Research Institute Of Chemical Technology	Compounds for inhibiting tnik and medical uses thereof

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DD211343A1 (de) *	1982-11-08	1984-07-11	Univ Ernst Moritz Arndt	Verfahren zur synthese von pyrazolen
EP0178035B1 (en) *	1984-05-12	1990-01-03	FISONS plc	Anti-inflammatory 1,n-diarylpyrazol-3-amines, compositions containing them and processes for their preparation

1987
- 1987-04-27 EP EP87303666A patent/EP0248523B1/en not_active Expired - Lifetime
- 1987-04-27 DE DE8787303666T patent/DE3773746D1/de not_active Expired - Fee Related
- 1987-05-05 FI FI871974A patent/FI871974L/fi not_active IP Right Cessation
- 1987-05-05 IL IL82421A patent/IL82421A0/xx unknown
- 1987-05-05 US US07/046,656 patent/US4803216A/en not_active Expired - Fee Related
- 1987-05-06 CA CA000536506A patent/CA1305157C/en not_active Expired - Fee Related
- 1987-05-06 NO NO871879A patent/NO871879L/no unknown
- 1987-05-06 NZ NZ220214A patent/NZ220214A/xx unknown
- 1987-05-06 DK DK231687A patent/DK231687A/da not_active Application Discontinuation
- 1987-05-07 PT PT84831A patent/PT84831B/pt not_active IP Right Cessation
- 1987-05-07 KR KR870004448A patent/KR870011101A/ko not_active Withdrawn
- 1987-05-07 AU AU72584/87A patent/AU595602B2/en not_active Ceased
- 1987-11-03 AT AT0290487A patent/AT390732B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA290487A (de)	1989-12-15
FI871974A7 (fi)	1987-11-08
AU595602B2 (en)	1990-04-05
EP0248523A1 (en)	1987-12-09
US4803216A (en)	1989-02-07
FI871974L (fi)	1987-11-08
IL82421A0 (en)	1987-11-30
AT390732B (de)	1990-06-25
EP0248523B1 (en)	1991-10-16
DE3773746D1 (en)	1991-11-21
NZ220214A (en)	1990-06-26
PT84831A (en)	1987-06-01
NO871879D0 (no)	1987-05-06
FI871974A0 (fi)	1987-05-05
DK231687D0 (da)	1987-05-06
KR870011101A (ko)	1987-12-21
PT84831B (pt)	1990-02-08
CA1305157C (en)	1992-07-14
DK231687A (da)	1987-11-08
AU7258487A (en)	1987-11-12

Publication	Publication Date	Title
NO871879L (no)	1987-11-09	Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser.
US4590189A (en)	1986-05-20	Condensed pyrrolinone derivatives, their production and use
US5428044A (en)	1995-06-27	Anti-inflammatory 4-aminophenyl derivatives
US5602152A (en)	1997-02-11	Benzoxepines
US5064837A (en)	1991-11-12	3-substituted-1-aryl-2(h)-quinolones and their pharmaceutical compositions
US5712294A (en)	1998-01-27	N-pyridyl carboxamides and derivatives
US4621089A (en)	1986-11-04	Pyrazolopyridine derivatives and their use in treating inflammation and allergic conditions
US4698344A (en)	1987-10-06	1-Heteroaryl-4-aryl-pyrazolin-5-ones for use as medicaments
US4612318A (en)	1986-09-16	CNS-depressant and analgesic tricyclo-[pyrazolo-[3,4-6]-pyridine] derivatives and pharmaceutical compositions thereof
US4914099A (en)	1990-04-03	Hydantoin derivatives as aldose reductase inhibitors
JP2740250B2 (ja)	1998-04-15	ヘテラ―脂肪族カルボクサミド誘導体、その製造方法、該化合物の中間体および該化合物を含有するロイコトリエン拮抗作用を有する薬学的組成物
US4572910A (en)	1986-02-25	Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings
US9120764B2 (en)	2015-09-01	Chromene derivatives
US6051570A (en)	2000-04-18	Benzimidazole derivatives as antiulcer agents, process for their preparation and pharmaceutical compositions containing them
US4565816A (en)	1986-01-21	Piperazine derivatives and pharmaceutical composition containing them
CS226021B2 (en)	1984-03-19	Method of presparing piperidine propylderivatives
US4088764A (en)	1978-05-09	Pharmaceutically active derivatives of 1-phenoxy-3-amino-propan-2-ol
NO164899B (no)	1990-08-20	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolylindolforbindelser.
EP0127371B1 (en)	1990-11-22	1,n-diaryl-4,5-dihydro-1h-pyrazol-3-amines, compositions containing them and methods for their preparation
US5051430A (en)	1991-09-24	3-(1H-indazol-3-yl)-4-pyridinamines
US4411907A (en)	1983-10-25	Antiinflammatory 3H-naphtho(1,2-d)imidazoles
NO832810L (no)	1984-02-06	1,3-dioksolo(4,5-g)-kinoliner og fremgangsmaate for deres fremstilling.
EP0287971B1 (en)	1993-02-24	Benzimidazole derivatives and process for their preparations
JPS62267269A (ja)	1987-11-19	ピラゾ−ル−３−アミン類
US4721718A (en)	1988-01-26	2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers