NO324698B1 - Nye forbindelser, farmasoytiske preparat inneholdende slike, fremgangsmate for deres fremstilling samt anvendelser derav - Google Patents
Nye forbindelser, farmasoytiske preparat inneholdende slike, fremgangsmate for deres fremstilling samt anvendelser derav Download PDFInfo
- Publication number
- NO324698B1 NO324698B1 NO20026064A NO20026064A NO324698B1 NO 324698 B1 NO324698 B1 NO 324698B1 NO 20026064 A NO20026064 A NO 20026064A NO 20026064 A NO20026064 A NO 20026064A NO 324698 B1 NO324698 B1 NO 324698B1
- Authority
- NO
- Norway
- Prior art keywords
- acetamide
- hydroxypropoxy
- phenyl
- amino
- piperidinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 24
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- -1 N-(2- {[(2S)-3 -({- [(4-chlorophenyl)methyl] -4-piperidinyl} amino)-2-hydroxypropoxy] - oxy} phenyl)acetamide Chemical compound 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 6
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 102000009410 Chemokine receptor Human genes 0.000 claims description 4
- 108050000299 Chemokine receptor Proteins 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- HCRCJAUNDNWDKN-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 HCRCJAUNDNWDKN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- JYNYZGTZSYGZFF-UHFFFAOYSA-N 2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Br)=CC=2)CC1 JYNYZGTZSYGZFF-UHFFFAOYSA-N 0.000 claims description 3
- OSBDKNMYPCZPAJ-UHFFFAOYSA-N 2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 OSBDKNMYPCZPAJ-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
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- UHWWMQGKINJTML-XMMPIXPASA-N n-[2-[(2r)-3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@](C)(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 UHWWMQGKINJTML-XMMPIXPASA-N 0.000 claims description 3
- XZZCEIOLUHBWLL-NRFANRHFSA-N n-[2-[(2s)-3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@@H](O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 XZZCEIOLUHBWLL-NRFANRHFSA-N 0.000 claims description 3
- FBMVIPOJAIEMEQ-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 FBMVIPOJAIEMEQ-UHFFFAOYSA-N 0.000 claims description 3
- SFSYBIMGDOACAY-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-5-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC(F)=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 SFSYBIMGDOACAY-UHFFFAOYSA-N 0.000 claims description 3
- DQKWBTYEFDDBCD-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 DQKWBTYEFDDBCD-UHFFFAOYSA-N 0.000 claims description 3
- MBQWSRZWBXESPI-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=C(F)C(F)=CC=2)CC1 MBQWSRZWBXESPI-UHFFFAOYSA-N 0.000 claims description 3
- MNBLPGMJPDFOBA-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(F)C(F)=C1 MNBLPGMJPDFOBA-UHFFFAOYSA-N 0.000 claims description 3
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- LYQPXPOTVRGEDB-UHFFFAOYSA-N n-[2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=CC(Br)=CC=2)CC1 LYQPXPOTVRGEDB-UHFFFAOYSA-N 0.000 claims description 3
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- XZZCEIOLUHBWLL-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 XZZCEIOLUHBWLL-UHFFFAOYSA-N 0.000 claims description 3
- OVEFNRNRCYLREF-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-5-cyanophenyl]acetamide Chemical compound CC(=O)NC1=CC(C#N)=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 OVEFNRNRCYLREF-UHFFFAOYSA-N 0.000 claims description 3
- XZZZCTNRNINFIV-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 XZZZCTNRNINFIV-UHFFFAOYSA-N 0.000 claims description 3
- KPPHYQMDMZRERL-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-6-methylphenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=CC=C1OCC(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 KPPHYQMDMZRERL-UHFFFAOYSA-N 0.000 claims description 3
- JREWIIXZKFBBRF-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 JREWIIXZKFBBRF-UHFFFAOYSA-N 0.000 claims description 3
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- DDKIBHNVQJBPOJ-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 DDKIBHNVQJBPOJ-UHFFFAOYSA-N 0.000 claims description 2
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- XXJAJULFILCYBG-UHFFFAOYSA-N n-[2-[3-[[1-[(3-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]-3,5-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C)=CC(C)=C1C(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=C(F)C=CC=2)CC1 XXJAJULFILCYBG-UHFFFAOYSA-N 0.000 claims description 2
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- UIJXHKXIOCDSEB-UHFFFAOYSA-N tert-butyl 3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(O)C1 UIJXHKXIOCDSEB-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
- 201000005539 vernal conjunctivitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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]
-
- 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
Applications Claiming Priority (3)
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SE0002331A SE0002331D0 (sv) | 2000-06-20 | 2000-06-20 | Novel compounds |
SE0004480A SE0004480D0 (sv) | 2000-12-05 | 2000-12-05 | Novel compounds |
PCT/SE2001/001377 WO2001098273A1 (en) | 2000-06-20 | 2001-06-14 | Novel compounds |
Publications (3)
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NO20026064D0 NO20026064D0 (no) | 2002-12-17 |
NO20026064L NO20026064L (no) | 2003-02-17 |
NO324698B1 true NO324698B1 (no) | 2007-12-03 |
Family
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NO20026064A NO324698B1 (no) | 2000-06-20 | 2002-12-17 | Nye forbindelser, farmasoytiske preparat inneholdende slike, fremgangsmate for deres fremstilling samt anvendelser derav |
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US (3) | US6911458B2 (pt) |
EP (1) | EP1299357A1 (pt) |
JP (1) | JP4022142B2 (pt) |
KR (1) | KR100799061B1 (pt) |
CN (1) | CN1307157C (pt) |
AR (1) | AR028948A1 (pt) |
AU (2) | AU7476301A (pt) |
BR (1) | BR0111667A (pt) |
CA (1) | CA2414095C (pt) |
CZ (1) | CZ20024146A3 (pt) |
EE (1) | EE05157B1 (pt) |
HU (1) | HUP0301187A3 (pt) |
IL (2) | IL153167A0 (pt) |
IS (1) | IS6658A (pt) |
MX (1) | MXPA02012425A (pt) |
MY (1) | MY136520A (pt) |
NO (1) | NO324698B1 (pt) |
NZ (1) | NZ523047A (pt) |
PL (1) | PL203936B1 (pt) |
RU (2) | RU2298550C2 (pt) |
SK (1) | SK17932002A3 (pt) |
WO (1) | WO2001098273A1 (pt) |
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TW200738635A (en) * | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
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-
2001
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- 2001-06-14 SK SK1793-2002A patent/SK17932002A3/sk not_active Application Discontinuation
- 2001-06-14 AU AU7476301A patent/AU7476301A/xx active Pending
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- 2001-06-14 PL PL366198A patent/PL203936B1/pl not_active IP Right Cessation
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- 2001-06-14 CN CNB018142141A patent/CN1307157C/zh not_active Expired - Fee Related
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