NO308994B1 - Corticotropin-frigjøringsfaktorantagonister, anvendelse og fremstilling derav, samt farmasøytisk preparat - Google Patents
Corticotropin-frigjøringsfaktorantagonister, anvendelse og fremstilling derav, samt farmasøytisk preparat Download PDFInfo
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- NO308994B1 NO308994B1 NO965237A NO965237A NO308994B1 NO 308994 B1 NO308994 B1 NO 308994B1 NO 965237 A NO965237 A NO 965237A NO 965237 A NO965237 A NO 965237A NO 308994 B1 NO308994 B1 NO 308994B1
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- Norway
- Prior art keywords
- alkyl
- ethyl
- methyl
- dimethyl
- phenoxy
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 7
- 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 title description 2
- 239000002769 corticotropin releasing factor antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 238000000034 method Methods 0.000 claims abstract description 43
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 40
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- 238000006243 chemical reaction Methods 0.000 claims description 35
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 34
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- 125000004076 pyridyl group Chemical group 0.000 claims description 16
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- PRHLXIOMJCBPHZ-UHFFFAOYSA-N n,n-diethyl-3,6-dimethyl-2-(2,4,6-trimethylphenoxy)pyridin-4-amine Chemical compound CCN(CC)C1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C PRHLXIOMJCBPHZ-UHFFFAOYSA-N 0.000 description 1
- UPZQMYJBMDTOPN-UHFFFAOYSA-N n-[2-(4-chloro-2,6-dimethylphenoxy)-6-methyl-4-(pentan-3-ylamino)pyridin-3-yl]acetamide Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1NC(C)=O UPZQMYJBMDTOPN-UHFFFAOYSA-N 0.000 description 1
- JORDCVXOMHYJNH-UHFFFAOYSA-N n-[6-methyl-4-(pentan-3-ylamino)-2-(2,4,6-trimethylphenoxy)pyridin-3-yl]acetamide Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1NC(C)=O JORDCVXOMHYJNH-UHFFFAOYSA-N 0.000 description 1
- CKLOCFUOUHTOQE-UHFFFAOYSA-N n-butyl-n-ethyl-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)pyrimidin-4-amine Chemical compound CCCCN(CC)C1=NC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C CKLOCFUOUHTOQE-UHFFFAOYSA-N 0.000 description 1
- JJUIFGPONBSLSD-UHFFFAOYSA-N n-butyl-n-ethyl-2,8-dimethyl-9-(2,4,6-trimethylphenyl)purin-6-amine Chemical compound CC1=NC=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C JJUIFGPONBSLSD-UHFFFAOYSA-N 0.000 description 1
- PIMIYBUSGIENNU-UHFFFAOYSA-N n-ethyl-3,6-dimethyl-2-(2,4,6-trimethylphenoxy)pyridin-4-amine Chemical compound CCNC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C PIMIYBUSGIENNU-UHFFFAOYSA-N 0.000 description 1
- SNDJAKRYNVNLTD-UHFFFAOYSA-N n-ethyl-3,6-dimethyl-2-(2,4,6-trimethylphenyl)sulfanylpyridin-4-amine Chemical compound CCNC1=CC(C)=NC(SC=2C(=CC(C)=CC=2C)C)=C1C SNDJAKRYNVNLTD-UHFFFAOYSA-N 0.000 description 1
- KKOJCBBVONUKJG-UHFFFAOYSA-N n-ethyl-n,3,6-trimethyl-2-(2,4,6-trimethylphenoxy)pyridin-4-amine Chemical compound CCN(C)C1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C KKOJCBBVONUKJG-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UFZNZKGKBWOSJG-UHFFFAOYSA-N purin-2-one Chemical class O=C1N=CC2=NC=NC2=N1 UFZNZKGKBWOSJG-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- ORKUYZDMEWAUEZ-UHFFFAOYSA-N pyrrolo[3,2-b]pyridin-2-one Chemical class N1=CC=CC2=NC(=O)C=C21 ORKUYZDMEWAUEZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 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
- 238000012916 structural analysis Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C07D213/69—Two or more oxygen atoms
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- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- 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
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25551494A | 1994-06-08 | 1994-06-08 | |
PCT/IB1995/000439 WO1995033750A1 (en) | 1994-06-08 | 1995-06-06 | Corticotropin releasing factor antagonists |
Publications (3)
Publication Number | Publication Date |
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NO965237D0 NO965237D0 (no) | 1996-12-06 |
NO965237L NO965237L (no) | 1997-02-06 |
NO308994B1 true NO308994B1 (no) | 2000-11-27 |
Family
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Application Number | Title | Priority Date | Filing Date |
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NO965237A NO308994B1 (no) | 1994-06-08 | 1996-12-06 | Corticotropin-frigjøringsfaktorantagonister, anvendelse og fremstilling derav, samt farmasøytisk preparat |
NO20002391A NO310234B1 (no) | 1994-06-08 | 2000-05-08 | Fremgangsmåte for fremstilling av corticotropin- frigjöringsfaktorantagonister |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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NO20002391A NO310234B1 (no) | 1994-06-08 | 2000-05-08 | Fremgangsmåte for fremstilling av corticotropin- frigjöringsfaktorantagonister |
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US (1) | US5962479A (ru) |
EP (1) | EP0764166B1 (ru) |
JP (3) | JP3193055B2 (ru) |
KR (2) | KR100418240B1 (ru) |
CN (2) | CN1049659C (ru) |
AT (1) | ATE196295T1 (ru) |
AU (1) | AU692548B2 (ru) |
BR (1) | BR9502708A (ru) |
CA (1) | CA2192354C (ru) |
CO (1) | CO4440627A1 (ru) |
CZ (1) | CZ293752B6 (ru) |
DE (1) | DE69518841T2 (ru) |
DK (1) | DK0764166T3 (ru) |
ES (1) | ES2150567T3 (ru) |
FI (2) | FI114469B (ru) |
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PT (1) | PT764166E (ru) |
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TW (2) | TW574214B (ru) |
UA (1) | UA71535C2 (ru) |
WO (1) | WO1995033750A1 (ru) |
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