NO313517B1 - 6-Fenylpyridyl-2-aminderivater, anvendelse av disse og farmasöytiske preparater inneholdende dem - Google Patents

6-Fenylpyridyl-2-aminderivater, anvendelse av disse og farmasöytiske preparater inneholdende dem Download PDF

Info

Publication number: NO313517B1
Authority: NO; Norway
Prior art keywords: phenyl; ylamine; pyridin; alkyl; methyl
Prior art date: 1996-12-06

Application number

NO19992725A

Other languages

English (en)

Norwegian (no)

Other versions

NO992725L (no

NO992725D0 (no

Inventor

Iii John Adams Lowe

Original Assignee

Pfizer

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.)

1996-12-06

Filing date

1999-06-04

Publication date

2002-10-14

1999-06-04 Application filed by Pfizer filed Critical Pfizer

1999-06-04 Publication of NO992725L publication Critical patent/NO992725L/no

1999-06-04 Publication of NO992725D0 publication Critical patent/NO992725D0/no

2002-10-14 Publication of NO313517B1 publication Critical patent/NO313517B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 89
-1 hydroxy, methyl Chemical group 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 23
125000003710 aryl alkyl group Chemical group 0.000 claims description 22
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 19
108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 19
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 19
241000124008 Mammalia Species 0.000 claims description 18
208000002193 Pain Diseases 0.000 claims description 17
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 16
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 16
230000001154 acute effect Effects 0.000 claims description 16
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 16
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 16
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 16
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
206010040070 Septic Shock Diseases 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
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239000001257 hydrogen Substances 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 9
201000011510 cancer Diseases 0.000 claims description 9
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238000002360 preparation method Methods 0.000 claims description 9
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MNUHYQZBNHDABI-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-6-amine Chemical group C1NCC2C(N)C21 MNUHYQZBNHDABI-UHFFFAOYSA-N 0.000 claims description 8
208000030507 AIDS Diseases 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 8
208000019901 Anxiety disease Diseases 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
208000000094 Chronic Pain Diseases 0.000 claims description 8
206010009900 Colitis ulcerative Diseases 0.000 claims description 8
206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 8
208000011231 Crohn disease Diseases 0.000 claims description 8
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208000007342 Diabetic Nephropathies Diseases 0.000 claims description 8
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 8
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208000010412 Glaucoma Diseases 0.000 claims description 8
206010019196 Head injury Diseases 0.000 claims description 8
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208000019695 Migraine disease Diseases 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 8
206010063837 Reperfusion injury Diseases 0.000 claims description 8
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206010044541 Traumatic shock Diseases 0.000 claims description 8
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125000003282 alkyl amino group Chemical group 0.000 claims description 8
230000036506 anxiety Effects 0.000 claims description 8
208000033679 diabetic kidney disease Diseases 0.000 claims description 8
206010015037 epilepsy Diseases 0.000 claims description 8
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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201000006417 multiple sclerosis Diseases 0.000 claims description 8
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230000016087 ovulation Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
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208000023105 Huntington disease Diseases 0.000 claims description 7
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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 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
230000004770 neurodegeneration Effects 0.000 claims description 7
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
206010029350 Neurotoxicity Diseases 0.000 claims description 6
206010044221 Toxic encephalopathy Diseases 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
230000007135 neurotoxicity Effects 0.000 claims description 6
231100000228 neurotoxicity Toxicity 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
206010013663 drug dependence Diseases 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
208000011117 substance-related disease Diseases 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
MWNICFXVCUVIBR-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethyl]-1-[2-(dimethylamino)ethyl]-3h-indol-2-one Chemical compound C12=CC=CC=C2N(CCN(C)C)C(=O)C1C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 MWNICFXVCUVIBR-UHFFFAOYSA-N 0.000 claims description 2
ZOMWHUFJIVHYTM-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethyl]-1-methyl-3h-indol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 ZOMWHUFJIVHYTM-UHFFFAOYSA-N 0.000 claims description 2
AFXPRGRPBFUARV-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethylidene]-1-[2-(dimethylamino)ethyl]indol-2-one Chemical compound C12=CC=CC=C2N(CCN(C)C)C(=O)C1=C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 AFXPRGRPBFUARV-UHFFFAOYSA-N 0.000 claims description 2
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
210000002569 neuron Anatomy 0.000 claims description 2
230000001988 toxicity Effects 0.000 claims description 2
231100000419 toxicity Toxicity 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
230000001225 therapeutic effect Effects 0.000 claims 3
125000003545 alkoxy group Chemical group 0.000 claims 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
RDUSFASPCBUTSL-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethylidene]-1-methylindol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1=C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 RDUSFASPCBUTSL-UHFFFAOYSA-N 0.000 claims 1
XPZYBFOYRKOKPL-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octan-8-ol Chemical compound C1NCC2CCC1C2O XPZYBFOYRKOKPL-UHFFFAOYSA-N 0.000 claims 1
JEIONJSEBLCOJW-UHFFFAOYSA-N 6-[4-[1-(1,3-benzodioxol-5-ylmethyl)piperidin-4-yl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C2CCN(CC=3C=C4OCOC4=CC=3)CC2)=N1 JEIONJSEBLCOJW-UHFFFAOYSA-N 0.000 claims 1
ULNUZJQBLXAHCQ-UHFFFAOYSA-N 8-[4-(6-aminopyridin-2-yl)phenyl]-3-(2-methylpropyl)-3-azabicyclo[3.2.1]octan-8-ol Chemical compound C1N(CC(C)C)CC2CCC1C2(O)C(C=C1)=CC=C1C1=CC=CC(N)=N1 ULNUZJQBLXAHCQ-UHFFFAOYSA-N 0.000 claims 1
IREJNWMYFOEDGE-UHFFFAOYSA-N 8-[4-(6-aminopyridin-2-yl)phenyl]-3-(furan-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-ol Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C2(O)C3CCC2CN(CC=2OC=CC=2)C3)=N1 IREJNWMYFOEDGE-UHFFFAOYSA-N 0.000 claims 1
MXNCJGDSGDBEBK-UHFFFAOYSA-N 8-[4-(6-aminopyridin-2-yl)phenyl]-3-benzyl-3-azabicyclo[3.2.1]octan-8-ol Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C2(O)C3CCC2CN(CC=2C=CC=CC=2)C3)=N1 MXNCJGDSGDBEBK-UHFFFAOYSA-N 0.000 claims 1
206010012335 Dependence Diseases 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000001786 isothiazolyl group Chemical group 0.000 claims 1
125000000842 isoxazolyl group Chemical group 0.000 claims 1
UHFXNKIOKXNMMJ-UHFFFAOYSA-N n-[2-[2-[2-(6-aminopyridin-2-yl)phenyl]ethyl]-4-phenylcyclohexyl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound NC1=CC=CC(C=2C(=CC=CC=2)CCC2C(CCC(C2)C=2C=CC=CC=2)NC2C3CNCC32)=N1 UHFXNKIOKXNMMJ-UHFFFAOYSA-N 0.000 claims 1
RISWCGKBVILZDK-UHFFFAOYSA-N n-[4-[4-(6-aminopyridin-2-yl)phenyl]piperidin-1-yl]acetamide Chemical compound C1CN(NC(=O)C)CCC1C1=CC=C(C=2N=C(N)C=CC=2)C=C1 RISWCGKBVILZDK-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 84
238000005160 1H NMR spectroscopy Methods 0.000 description 84
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 65
238000006243 chemical reaction Methods 0.000 description 64
239000000243 solution Substances 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
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238000010992 reflux Methods 0.000 description 35
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 33
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235000011152 sodium sulphate Nutrition 0.000 description 32
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239000003054 catalyst Substances 0.000 description 7
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Classifications

- C—CHEMISTRY; METALLURGY
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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
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General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Ophthalmology & Optometry (AREA)
Psychiatry (AREA)
Hematology (AREA)
Rheumatology (AREA)
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Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
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NO19992725A 1996-12-06 1999-06-04 6-Fenylpyridyl-2-aminderivater, anvendelse av disse og farmasöytiske preparater inneholdende dem NO313517B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3279396P	1996-12-06	1996-12-06
PCT/IB1997/001446 WO1998024766A1 (en)	1996-12-06	1997-11-17	6-phenylpyridyl-2-amine derivatives useful as nos inhibitors

Publications (3)

Publication Number	Publication Date
NO992725L NO992725L (no)	1999-06-04
NO992725D0 NO992725D0 (no)	1999-06-04
NO313517B1 true NO313517B1 (no)	2002-10-14

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ID=21866837

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19992725A NO313517B1 (no)	1996-12-06	1999-06-04	6-Fenylpyridyl-2-aminderivater, anvendelse av disse og farmasöytiske preparater inneholdende dem

Country Status (42)

Country	Link
US (3)	US6235750B1 (cs)
EP (1)	EP0946512B1 (cs)
JP (2)	JP3604399B2 (cs)
KR (1)	KR100360633B1 (cs)
CN (1)	CN1117077C (cs)
AP (1)	AP848A (cs)
AR (1)	AR010331A1 (cs)
AT (1)	ATE251612T1 (cs)
AU (2)	AU4791797A (cs)
BG (1)	BG103540A (cs)
BR (1)	BR9714381A (cs)
CA (1)	CA2273479C (cs)
CZ (1)	CZ293863B6 (cs)
DE (1)	DE69725465T2 (cs)
DK (1)	DK0946512T3 (cs)
DZ (1)	DZ2361A1 (cs)
EA (1)	EA002907B1 (cs)
ES (1)	ES2206691T3 (cs)
HN (2)	HN1997000027A (cs)
HR (1)	HRP970664A2 (cs)
HU (1)	HUP0001848A3 (cs)
ID (1)	ID19056A (cs)
IL (1)	IL130111A0 (cs)
IS (1)	IS5053A (cs)
MA (1)	MA26453A1 (cs)
NO (1)	NO313517B1 (cs)
NZ (1)	NZ335733A (cs)
OA (1)	OA11123A (cs)
PA (1)	PA8442201A1 (cs)
PE (1)	PE46499A1 (cs)
PL (1)	PL333918A1 (cs)
PT (1)	PT946512E (cs)
SI (1)	SI0946512T1 (cs)
SK (1)	SK70899A3 (cs)
TN (1)	TNSN97198A1 (cs)
TR (1)	TR199901259T2 (cs)
TW (1)	TW491840B (cs)
UA (1)	UA59379C2 (cs)
UY (1)	UY24799A1 (cs)
WO (1)	WO1998024766A1 (cs)
YU (1)	YU25399A (cs)
ZA (1)	ZA9710906B (cs)

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FR2791674A1 (fr) *	1999-04-02	2000-10-06	Sod Conseils Rech Applic	Nouveaux derives de 2-aminopyridines, leur utilisation en tant que medicaments et compositions pharmaceutiques les contenant
AR019190A1 (es) *	1998-07-08	2001-12-26	Sod Conseils Rech Applic	Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos
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SE9803710L (sv)	1998-09-25	2000-03-26	A & Science Invest Ab	Användning av vissa substanser för behandling av nervrotsskador
CZ20013036A3 (cs)	1999-02-25	2002-03-13	Pfizer Products Inc.	2-aminopyridiny obsahující jako substituenty kondenzované kruhové skupiny
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FR2804429B1 (fr) *	2000-01-31	2003-05-09	Adir	Nouveaux derives de 4-sulfonamides piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
AU2002303264A1 (en) *	2001-04-09	2002-10-21	Bristol-Myers Squibb Company	Fused heterocyclic inhibitors of factor xa
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US8633175B2 (en)	2006-08-09	2014-01-21	Glaxosmithkline Llc	Compounds as antagonists or inverse agonists at opioid receptors
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US8835437B2 (en)	2007-06-08	2014-09-16	Janssen Pharmaceutica N.V.	Piperidine/piperazine derivatives
JO2972B1 (en)	2007-06-08	2016-03-15	جانسين فارماسوتيكا ان. في	Piperidine / piperazine derivatives
WO2008148851A1 (en)	2007-06-08	2008-12-11	Janssen Pharmaceutica N.V.	Piperidine/piperazine derivatives
JP5579170B2 (ja)	2008-06-05	2014-08-27	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	Ｄｇａｔ阻害剤とｐｐａｒ作動薬を含有する薬剤組み合わせ物
UA105182C2 (ru)	2008-07-03	2014-04-25	Ньюрексон, Інк.	Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
EP2404902A1 (en) *	2009-03-05	2012-01-11	Shionogi&Co., Ltd.	Piperidine and pyrrolidine derivatives having npy y5 receptor antagonism
US11013844B2 (en) *	2014-11-20	2021-05-25	City Of Hope	Treatment device for plasma virus inactivation
CN118384166A (zh)	2016-08-12	2024-07-26	阿西纳斯公司	用于调节激酶级联的联芳组合物和方法
BR112020005489A2 (pt)	2017-09-22	2020-09-24	Jubilant Epipad Llc,	composto da fórmula (i), composto de fórmula (ii), composto de fórmula (iii), processo de preparação de compostos de fórmula (i), processo de preparação de compostos de fórmula (ii), processo de preparação de compostos de fórmula (iii), composição farmacêutica, método para inibir uma ou mais famílias pad em uma célula, método para tratar uma afeção mediada por um ou mais pads, utilização do composto, método para o tratamento e/ou prevenção de uma afeção mediada por um ou mais distúrbios da família pad, método para o tratamento de artrite reumatoide e método de tratamento de câncer
SG11202003463XA (en)	2017-10-18	2020-05-28	Jubilant Epipad LLC	Imidazo-pyridine compounds as pad inhibitors
EP3707135A1 (en)	2017-11-06	2020-09-16	Jubilant Prodel LLC	Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation
IL274762B2 (en)	2017-11-24	2023-10-01	Jubilant Episcribe Llc	Novel heterocyclic compounds as prmt5 inhibitors
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1997
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- 1997-11-17 SK SK708-99A patent/SK70899A3/sk unknown
- 1997-11-17 NZ NZ335733A patent/NZ335733A/xx unknown
- 1997-11-17 DK DK97910587T patent/DK0946512T3/da active
- 1997-11-17 IL IL13011197A patent/IL130111A0/xx unknown
- 1997-11-17 AU AU47917/97A patent/AU4791797A/en not_active Abandoned
- 1997-11-17 YU YU25399A patent/YU25399A/sh unknown
- 1997-11-17 EA EA199900448A patent/EA002907B1/ru not_active IP Right Cessation
- 1997-11-17 KR KR1019997004981A patent/KR100360633B1/ko not_active IP Right Cessation
- 1997-11-17 SI SI9730597T patent/SI0946512T1/xx unknown
- 1997-11-18 HN HN1997000149A patent/HN1997000149A/es unknown
- 1997-11-22 TW TW086117501A patent/TW491840B/zh active
- 1997-12-01 PE PE1997001080A patent/PE46499A1/es not_active Application Discontinuation
- 1997-12-03 DZ DZ970211A patent/DZ2361A1/xx active
- 1997-12-03 TN TNTNSN97198A patent/TNSN97198A1/fr unknown
- 1997-12-03 MA MA24884A patent/MA26453A1/fr unknown
- 1997-12-03 UY UY24799A patent/UY24799A1/es unknown
- 1997-12-04 ZA ZA9710906A patent/ZA9710906B/xx unknown
- 1997-12-04 PA PA19978442201A patent/PA8442201A1/es unknown
- 1997-12-04 AP APAP/P/1997/001156A patent/AP848A/en active
- 1997-12-04 HR HR60/032,793A patent/HRP970664A2/hr not_active Application Discontinuation
- 1997-12-04 AR ARP970105713A patent/AR010331A1/es not_active Application Discontinuation
- 1997-12-05 ID IDP973838A patent/ID19056A/id unknown
1999
- 1999-05-18 IS IS5053A patent/IS5053A/is unknown
- 1999-06-01 OA OA9900115A patent/OA11123A/en unknown
- 1999-06-03 US US09/325,480 patent/US6235750B1/en not_active Expired - Fee Related
- 1999-06-04 NO NO19992725A patent/NO313517B1/no unknown
- 1999-06-30 BG BG103540A patent/BG103540A/bg unknown
2001
- 2001-03-08 US US09/802,086 patent/US20020032191A1/en not_active Abandoned
- 2001-09-13 AU AU72050/01A patent/AU766080B2/en not_active Ceased
- 2001-09-27 US US09/965,564 patent/US20020103227A1/en not_active Abandoned
2004
- 2004-06-24 JP JP2004186311A patent/JP2005170924A/ja active Pending

Also Published As

Publication number	Publication date
CN1239952A (zh)	1999-12-29
TNSN97198A1 (fr)	2005-03-15
AP848A (en)	2000-06-09
PE46499A1 (es)	1999-05-12
IS5053A (is)	1999-05-18
HRP970664A2 (en)	1998-10-31
JP2000505814A (ja)	2000-05-16
DZ2361A1 (fr)	2002-12-28
HUP0001848A2 (hu)	2001-04-28
CZ293863B6 (cs)	2004-08-18
CZ201799A3 (cs)	2000-07-12
BG103540A (bg)	2000-12-29
ES2206691T3 (es)	2004-05-16
ID19056A (id)	1998-06-11
HUP0001848A3 (en)	2002-03-28
CN1117077C (zh)	2003-08-06
PA8442201A1 (es)	2000-05-24
ATE251612T1 (de)	2003-10-15
US6235750B1 (en)	2001-05-22
US20020103227A1 (en)	2002-08-01
IL130111A0 (en)	2000-06-01
CA2273479A1 (en)	1998-06-11
EA199900448A1 (ru)	2000-02-28
MA26453A1 (fr)	2004-12-20
NO992725L (no)	1999-06-04
DK0946512T3 (da)	2004-01-12
DE69725465D1 (de)	2003-11-13
UY24799A1 (es)	2001-08-27
YU25399A (sh)	2001-07-10
CA2273479C (en)	2006-02-07
AU7205001A (en)	2001-11-15
ZA9710906B (en)	1999-06-09
PL333918A1 (en)	2000-01-31
TW491840B (en)	2002-06-21
BR9714381A (pt)	2000-05-02
NO992725D0 (no)	1999-06-04
US20020032191A1 (en)	2002-03-14
JP3604399B2 (ja)	2004-12-22
AR010331A1 (es)	2000-06-07
NZ335733A (en)	2001-01-26
KR100360633B1 (ko)	2002-11-13
HN1997000027A (es)	1997-06-05
EP0946512B1 (en)	2003-10-08
HN1997000149A (es)	1997-12-26
PT946512E (pt)	2004-01-30
EA002907B1 (ru)	2002-10-31
JP2005170924A (ja)	2005-06-30
UA59379C2 (uk)	2003-09-15
DE69725465T2 (de)	2004-05-06
SI0946512T1 (en)	2004-04-30
AP9701156A0 (en)	1998-01-31
KR20000057413A (ko)	2000-09-15
WO1998024766A1 (en)	1998-06-11
OA11123A (en)	2003-04-07
TR199901259T2 (xx)	1999-08-23
EP0946512A1 (en)	1999-10-06
SK70899A3 (en)	2002-04-04
AU766080B2 (en)	2003-10-09
AU4791797A (en)	1998-06-29

Publication	Publication Date	Title
NO313517B1 (no)	2002-10-14	6-Fenylpyridyl-2-aminderivater, anvendelse av disse og farmasöytiske preparater inneholdende dem
AP1213A (en)	2003-10-07	2-aminopyridines containing fused ring substituents.
JPH11510513A (ja)	1999-09-14	６―フェニルピリジル―２―アミン誘導体
KR20000070803A (ko)	2000-11-25	2-아미노-6-(2-치환된-4-페녹시)-치환된-피리딘
EP1699783A1 (en)	2006-09-13	Opioid receptor antagonists
AU8458698A (en)	1999-03-22	Branched alkoxy-subsituted 2-aminopyridines as nos inhibitors
AP1208A (en)	2003-09-29	2-Aminopyridines containing fused ring substituents
US20040142924A1 (en)	2004-07-22	6-Phenylpyridyl-2-amine derivatives useful as NOS inhibitors
US20010049379A1 (en)	2001-12-06	2-aminopyridines containing fused ring substituents
CZ20004494A3 (cs)	2001-05-16	2-aminopyridiny obsahující kondenzované cyklické substituenty jako inhibitory synthasy oxidu dusnatého