NO324932B1 - 1,2,3,4-Tetrahydroisokinolin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende slike samt slike forbindelser anvendt til fremstilling av medikament for behandling av sykdommer - Google Patents
1,2,3,4-Tetrahydroisokinolin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende slike samt slike forbindelser anvendt til fremstilling av medikament for behandling av sykdommer Download PDFInfo
- Publication number
- NO324932B1 NO324932B1 NO20024339A NO20024339A NO324932B1 NO 324932 B1 NO324932 B1 NO 324932B1 NO 20024339 A NO20024339 A NO 20024339A NO 20024339 A NO20024339 A NO 20024339A NO 324932 B1 NO324932 B1 NO 324932B1
- Authority
- NO
- Norway
- Prior art keywords
- benzyl
- dimethoxy
- acetamide
- dihydro
- isoquinolin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 11
- 238000011282 treatment Methods 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title abstract description 16
- 201000010099 disease Diseases 0.000 title description 5
- 239000004480 active ingredient Substances 0.000 claims abstract 4
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- -1 lower-alkenyl Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 29
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
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- QDVAKWOYMQNGGI-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-methylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCN1CC(=O)N(C)CC1=CC=CC=C1 QDVAKWOYMQNGGI-UHFFFAOYSA-N 0.000 description 1
- DLZVDBYNJQVSNK-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 DLZVDBYNJQVSNK-UHFFFAOYSA-N 0.000 description 1
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- JCMWNICXFYUVHB-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-6-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OCC=3C=CC=CC=3)C=C2CCN1CC(=O)NCC1=CC=CC=C1 JCMWNICXFYUVHB-UHFFFAOYSA-N 0.000 description 1
- YJNWEXBIPHHTSL-UHFFFAOYSA-N n-benzyl-2-[1-[(3-bromo-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(Br)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 YJNWEXBIPHHTSL-UHFFFAOYSA-N 0.000 description 1
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- RRBYCHHICVPEJB-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(3-methoxy-4-pyrimidin-2-yloxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC=2N=CC=CN=2)C(OC)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 RRBYCHHICVPEJB-UHFFFAOYSA-N 0.000 description 1
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- CEUYUUKQQOETJF-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(4-methoxy-3-pyrimidin-2-yloxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC=2N=CC=CN=2)C(OC)=CC=C1CC(C1=CC(OC)=C(OC)C=C1CC1)N1CC(=O)NCC1=CC=CC=C1 CEUYUUKQQOETJF-UHFFFAOYSA-N 0.000 description 1
- QFHFJDFMLQDNNR-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[[3-methoxy-4-(2-methylpropoxy)phenyl]methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OCC(C)C)C(OC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 QFHFJDFMLQDNNR-UHFFFAOYSA-N 0.000 description 1
- NQXVNLHPEJBZAT-UHFFFAOYSA-N n-benzyl-n-methylacetamide Chemical compound CC(=O)N(C)CC1=CC=CC=C1 NQXVNLHPEJBZAT-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 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
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- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
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- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000007925 phenylethylamine derivatives Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 208000021310 pituitary gland adenoma Diseases 0.000 description 1
- 208000020351 pituitary gland basophil adenoma Diseases 0.000 description 1
- 208000017402 pituitary gland disease Diseases 0.000 description 1
- 208000010916 pituitary tumor Diseases 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 208000026961 psychosexual disease Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 208000023516 stroke disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 208000009935 visceral pain Diseases 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Anesthesiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP0002245 | 2000-03-14 | ||
PCT/EP2001/002733 WO2001068609A1 (en) | 2000-03-14 | 2001-03-12 | 1,2,3,4-tetrahydroisoquinoline derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20024339D0 NO20024339D0 (no) | 2002-09-11 |
NO20024339L NO20024339L (no) | 2002-09-11 |
NO324932B1 true NO324932B1 (no) | 2008-01-07 |
Family
ID=8163870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20024339A NO324932B1 (no) | 2000-03-14 | 2002-09-11 | 1,2,3,4-Tetrahydroisokinolin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende slike samt slike forbindelser anvendt til fremstilling av medikament for behandling av sykdommer |
Country Status (18)
Country | Link |
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US (1) | US6703392B2 (ja) |
JP (1) | JP4009460B2 (ja) |
KR (2) | KR20070087103A (ja) |
CN (1) | CN100393703C (ja) |
AT (1) | ATE286500T1 (ja) |
AU (2) | AU2001260113B2 (ja) |
BR (1) | BRPI0109200B8 (ja) |
CA (1) | CA2402431C (ja) |
DE (1) | DE60108236T2 (ja) |
ES (1) | ES2234840T3 (ja) |
HU (1) | HU227811B1 (ja) |
IL (2) | IL150986A0 (ja) |
MX (1) | MXPA02008797A (ja) |
NO (1) | NO324932B1 (ja) |
NZ (1) | NZ520624A (ja) |
PT (1) | PT1274687E (ja) |
WO (1) | WO2001068609A1 (ja) |
ZA (1) | ZA200206467B (ja) |
Families Citing this family (93)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1353918B1 (en) * | 2000-11-28 | 2005-01-12 | Smithkline Beecham Plc | Morpholine derivatives as antagonists of orexin receptors |
GB0126292D0 (en) | 2001-11-01 | 2002-01-02 | Smithkline Beecham Plc | Compounds |
GB0130388D0 (en) * | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
CN1332942C (zh) * | 2002-10-11 | 2007-08-22 | 埃科特莱茵药品有限公司 | 磺酰基氨基-乙酸衍生物及其作为阿立新受体拮抗剂的应用 |
GB0225884D0 (en) * | 2002-11-06 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
AU2004215409B2 (en) * | 2003-02-24 | 2008-11-20 | Merck Sharp & Dohme Corp. | Aminocyclopentyl fused heterotricylicamide modulators of chemokine receptor activity |
EP1611104B1 (en) * | 2003-03-26 | 2009-07-01 | Actelion Pharmaceuticals Ltd. | Tetrahydroisoquinolyl acetamide derivatives for use as orexin receptor antagonists |
US7321065B2 (en) * | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
CN1780820A (zh) * | 2003-04-28 | 2006-05-31 | 埃科特莱茵药品有限公司 | 作为阿立新受体拮抗剂的喹喔啉-3-酮衍生物 |
CN1902177A (zh) | 2003-09-22 | 2007-01-24 | 万有制药株式会社 | 新哌啶衍生物 |
US20100048513A1 (en) | 2008-08-20 | 2010-02-25 | Hawkins Michael J | Novel inhibitors of chymase |
BRPI0507052A (pt) * | 2004-01-23 | 2007-06-12 | Janssen Pharmaceutica Nv | inibidores de quìnase |
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CA2402431A1 (en) | 2001-09-20 |
HUP0300207A2 (en) | 2003-05-28 |
CN100393703C (zh) | 2008-06-11 |
DE60108236D1 (de) | 2005-02-10 |
NO20024339D0 (no) | 2002-09-11 |
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DE60108236T2 (de) | 2005-12-22 |
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PT1274687E (pt) | 2005-04-29 |
KR20020080465A (ko) | 2002-10-23 |
MXPA02008797A (es) | 2005-09-08 |
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ATE286500T1 (de) | 2005-01-15 |
ZA200206467B (en) | 2003-11-13 |
CA2402431C (en) | 2009-10-06 |
HUP0300207A3 (en) | 2005-07-28 |
CN1416420A (zh) | 2003-05-07 |
JP4009460B2 (ja) | 2007-11-14 |
AU2001260113B2 (en) | 2006-04-06 |
KR20070087103A (ko) | 2007-08-27 |
KR100842698B1 (ko) | 2008-07-01 |
IL150986A0 (en) | 2003-02-12 |
US6703392B2 (en) | 2004-03-09 |
WO2001068609B1 (en) | 2002-02-21 |
NZ520624A (en) | 2004-02-27 |
HU227811B1 (en) | 2012-03-28 |
ES2234840T3 (es) | 2005-07-01 |
BRPI0109200B8 (pt) | 2021-05-25 |
WO2001068609A1 (en) | 2001-09-20 |
BRPI0109200B1 (pt) | 2015-08-11 |
NO20024339L (no) | 2002-09-11 |
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