ZA200609972B - Highly selective novel amidation method - Google Patents
Highly selective novel amidation method Download PDFInfo
- Publication number
- ZA200609972B ZA200609972B ZA200609972A ZA200609972A ZA200609972B ZA 200609972 B ZA200609972 B ZA 200609972B ZA 200609972 A ZA200609972 A ZA 200609972A ZA 200609972 A ZA200609972 A ZA 200609972A ZA 200609972 B ZA200609972 B ZA 200609972B
- Authority
- ZA
- South Africa
- Prior art keywords
- composition
- tetrahydro
- chloro
- dimethylpropyl
- acetoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 69
- 230000009435 amidation Effects 0.000 title description 3
- 238000007112 amidation reaction Methods 0.000 title description 3
- -1 aliphatic cyclic carboxamide Chemical class 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 34
- YFNOTMRKVGZZNF-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetate Chemical compound OC(=O)CC1CCNCC1 YFNOTMRKVGZZNF-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- 239000012535 impurity Substances 0.000 claims description 18
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 17
- 206010053159 Organ failure Diseases 0.000 claims description 16
- 239000000539 dimer Substances 0.000 claims description 16
- 230000004768 organ dysfunction Effects 0.000 claims description 15
- 210000002027 skeletal muscle Anatomy 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 11
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims description 11
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims description 11
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical group CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 18
- 229940126062 Compound A Drugs 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 7
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- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
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- 230000003213 activating effect Effects 0.000 description 4
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- 238000002425 crystallisation Methods 0.000 description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
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- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ADSALMJPJUKESW-UHFFFAOYSA-N beta-Homoproline Chemical compound OC(=O)CC1CCCN1 ADSALMJPJUKESW-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- IYDUFJOXYMLYNM-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetic acid;chloride Chemical compound [Cl-].OC(=O)CC1CC[NH2+]CC1 IYDUFJOXYMLYNM-UHFFFAOYSA-N 0.000 description 1
- OUENRUZPZZFMCA-UHFFFAOYSA-N 2-pyrrolidin-1-ium-3-ylacetate Chemical compound OC(=O)CC1CCNC1 OUENRUZPZZFMCA-UHFFFAOYSA-N 0.000 description 1
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- AYRHHRXKZJGDSA-UHFFFAOYSA-N 3-piperidin-1-ium-2-ylpropanoate Chemical compound OC(=O)CCC1CCCCN1 AYRHHRXKZJGDSA-UHFFFAOYSA-N 0.000 description 1
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- AUYQMCCWFNSFGV-UHFFFAOYSA-N 3-piperidin-1-ium-4-ylpropanoate Chemical compound OC(=O)CCC1CCNCC1 AUYQMCCWFNSFGV-UHFFFAOYSA-N 0.000 description 1
- HIDODKLFTVMWQL-UHFFFAOYSA-N 3-pyrrolidin-1-ium-2-ylpropanoate Chemical compound OC(=O)CCC1CCCN1 HIDODKLFTVMWQL-UHFFFAOYSA-N 0.000 description 1
- VQCUMONTEGWEIX-UHFFFAOYSA-N 3-pyrrolidin-3-ylpropanoic acid Chemical compound OC(=O)CCC1CCNC1 VQCUMONTEGWEIX-UHFFFAOYSA-N 0.000 description 1
- DJZHWXSZBAXITL-UHFFFAOYSA-N 4-(azepan-2-yl)butanoic acid Chemical compound OC(=O)CCCC1CCCCCN1 DJZHWXSZBAXITL-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 description 1
- 229960003856 argatroban Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OPFURXRZISKMJV-UHFFFAOYSA-N azepan-1-ium-2-carboxylate Chemical compound OC(=O)C1CCCCCN1 OPFURXRZISKMJV-UHFFFAOYSA-N 0.000 description 1
- DXCWXFLBYQNTOP-UHFFFAOYSA-N azepan-1-ium-3-carboxylate Chemical compound OC(=O)C1CCCCNC1 DXCWXFLBYQNTOP-UHFFFAOYSA-N 0.000 description 1
- BCVGGQNBSCMMPV-UHFFFAOYSA-N azepane-4-carboxylic acid Chemical compound OC(=O)C1CCCNCC1 BCVGGQNBSCMMPV-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 229960000873 enalapril Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000000275 quality assurance Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010898 silica gel chromatography 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
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004174417 | 2004-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200609972B true ZA200609972B (en) | 2008-08-27 |
Family
ID=34970324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200609972A ZA200609972B (en) | 2004-06-11 | 2005-06-10 | Highly selective novel amidation method |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20070238721A1 (de) |
| EP (1) | EP1753752A1 (de) |
| JP (1) | JP2008501629A (de) |
| CN (1) | CN101001854A (de) |
| AU (1) | AU2005252111A1 (de) |
| BR (1) | BRPI0511877A (de) |
| CA (1) | CA2569686A1 (de) |
| CR (1) | CR8803A (de) |
| IL (1) | IL179308A0 (de) |
| MA (1) | MA28688B1 (de) |
| MX (1) | MXPA06014152A (de) |
| NO (1) | NO20070123L (de) |
| RU (1) | RU2006147285A (de) |
| TW (1) | TW200604187A (de) |
| WO (1) | WO2005121133A1 (de) |
| ZA (1) | ZA200609972B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2245218B1 (de) | 2008-02-25 | 2019-06-19 | SixPoint Materials, Inc. | Verfahren zur herstellung von gruppe-iii-nitridwafer und gruppe-iii-nitridwafer |
| DE102008054612A1 (de) * | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
| TWI774767B (zh) * | 2017-05-12 | 2022-08-21 | 瑞士商多蒂孔股份有限公司 | 茚烷衍生物及其在有機電子產品的用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2140003A (en) * | 1983-04-13 | 1984-11-21 | Shell Int Research | Azetidine derivatives suitable for inducing male sterility in plants |
| JP3479796B2 (ja) * | 1995-09-13 | 2003-12-15 | 武田薬品工業株式会社 | ベンゾオキサゼピン化合物 |
| ES2158344T3 (es) * | 1995-09-13 | 2001-09-01 | Takeda Chemical Industries Ltd | Compuestos benzoxazepinicos, su produccion y uso como agentes reductores de lipidos. |
| JP4138299B2 (ja) * | 2000-11-09 | 2008-08-27 | 武田薬品工業株式会社 | 高密度リポタンパク−コレステロール上昇剤 |
| CA2428669A1 (en) * | 2000-11-09 | 2002-05-16 | Takeda Chemical Industries, Ltd. | High-density lipoprotein-cholesterol level elevating agent |
| ATE279423T1 (de) * | 2001-04-30 | 2004-10-15 | Lupin Lab Ltd | Ein verfahren zur herstellung von natrium fosinopril |
-
2005
- 2005-06-10 RU RU2006147285/04A patent/RU2006147285A/ru not_active Application Discontinuation
- 2005-06-10 MX MXPA06014152A patent/MXPA06014152A/es not_active Application Discontinuation
- 2005-06-10 CA CA002569686A patent/CA2569686A1/en not_active Abandoned
- 2005-06-10 AU AU2005252111A patent/AU2005252111A1/en not_active Abandoned
- 2005-06-10 US US11/628,906 patent/US20070238721A1/en not_active Abandoned
- 2005-06-10 ZA ZA200609972A patent/ZA200609972B/en unknown
- 2005-06-10 EP EP05751255A patent/EP1753752A1/de not_active Withdrawn
- 2005-06-10 TW TW094119234A patent/TW200604187A/zh unknown
- 2005-06-10 WO PCT/JP2005/011091 patent/WO2005121133A1/en active Application Filing
- 2005-06-10 CN CNA2005800268866A patent/CN101001854A/zh active Pending
- 2005-06-10 JP JP2006549745A patent/JP2008501629A/ja active Pending
- 2005-06-10 BR BRPI0511877-8A patent/BRPI0511877A/pt not_active IP Right Cessation
-
2006
- 2006-11-15 IL IL179308A patent/IL179308A0/en unknown
- 2006-12-11 CR CR8803A patent/CR8803A/es not_active Application Discontinuation
- 2006-12-28 MA MA29572A patent/MA28688B1/fr unknown
-
2007
- 2007-01-08 NO NO20070123A patent/NO20070123L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1753752A1 (de) | 2007-02-21 |
| WO2005121133A1 (en) | 2005-12-22 |
| TW200604187A (en) | 2006-02-01 |
| AU2005252111A1 (en) | 2005-12-22 |
| CA2569686A1 (en) | 2005-12-22 |
| IL179308A0 (en) | 2007-03-08 |
| CN101001854A (zh) | 2007-07-18 |
| CR8803A (es) | 2007-04-20 |
| MA28688B1 (fr) | 2007-06-01 |
| US20070238721A1 (en) | 2007-10-11 |
| MXPA06014152A (es) | 2007-01-29 |
| NO20070123L (no) | 2007-03-07 |
| BRPI0511877A (pt) | 2008-01-15 |
| JP2008501629A (ja) | 2008-01-24 |
| RU2006147285A (ru) | 2008-07-20 |
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