DE19913699A1 - Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-Dehydropiperidinen - Google Patents
Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-DehydropiperidinenInfo
- Publication number
- DE19913699A1 DE19913699A1 DE19913699A DE19913699A DE19913699A1 DE 19913699 A1 DE19913699 A1 DE 19913699A1 DE 19913699 A DE19913699 A DE 19913699A DE 19913699 A DE19913699 A DE 19913699A DE 19913699 A1 DE19913699 A1 DE 19913699A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- general formula
- hydrogen
- compound
- iii
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims abstract description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims abstract description 4
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical class C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims abstract description 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 101150096839 Fcmr gene Proteins 0.000 claims abstract description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims abstract description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract 2
- 239000001569 carbon dioxide Substances 0.000 claims abstract 2
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- -1 benzolsulfonyl Chemical group 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000006823 (C1-C6) acyl group Chemical group 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006027 Birch reduction reaction Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OMGHIGVFLOPEHJ-UHFFFAOYSA-N 2,5-dihydro-1h-pyrrol-1-ium-2-carboxylate Chemical compound OC(=O)C1NCC=C1 OMGHIGVFLOPEHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229960002591 hydroxyproline Drugs 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YZSOPZXHDQUUJP-BYPYZUCNSA-N (2s)-2-(1h-imidazol-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=NC=CN1 YZSOPZXHDQUUJP-BYPYZUCNSA-N 0.000 description 1
- XGUIFUMAHBYCME-YFKPBYRVSA-N (2s)-2-(1h-pyrrol-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CN1 XGUIFUMAHBYCME-YFKPBYRVSA-N 0.000 description 1
- BURVSCKWRUZTPY-YFKPBYRVSA-N (2s)-2-(cyclobutylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1CCC1 BURVSCKWRUZTPY-YFKPBYRVSA-N 0.000 description 1
- LDUWTIUXPVCEQF-LURJTMIESA-N (2s)-2-(cyclopentylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1CCCC1 LDUWTIUXPVCEQF-LURJTMIESA-N 0.000 description 1
- VVDBQHCKPZBJPG-YFKPBYRVSA-N (2s)-2-(furan-2-ylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1=CC=CO1 VVDBQHCKPZBJPG-YFKPBYRVSA-N 0.000 description 1
- MRTPISKDZDHEQI-YFKPBYRVSA-N (2s)-2-(tert-butylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC(C)(C)C MRTPISKDZDHEQI-YFKPBYRVSA-N 0.000 description 1
- NPDBDJFLKKQMCM-SCSAIBSYSA-N (2s)-2-amino-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)[C@H](N)C(O)=O NPDBDJFLKKQMCM-SCSAIBSYSA-N 0.000 description 1
- WAMWSIDTKSNDCU-ZETCQYMHSA-N (2s)-2-azaniumyl-2-cyclohexylacetate Chemical compound OC(=O)[C@@H](N)C1CCCCC1 WAMWSIDTKSNDCU-ZETCQYMHSA-N 0.000 description 1
- XGUXJMWPVJQIHI-YFKPBYRVSA-N (2s)-2-azaniumyl-3-cyclopropylpropanoate Chemical compound [O-]C(=O)[C@@H]([NH3+])CC1CC1 XGUXJMWPVJQIHI-YFKPBYRVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VYKAFBPZJHOYQY-UHFFFAOYSA-N 1-methoxycarbonyl-2,5-dihydropyrrole-2-carboxylic acid Chemical compound COC(=O)N1CC=CC1C(O)=O VYKAFBPZJHOYQY-UHFFFAOYSA-N 0.000 description 1
- LTHGZYQCFFPTAJ-UHFFFAOYSA-N 2-(1-adamantylamino)acetic acid Chemical compound C1C(C2)CC3CC2CC1(NCC(=O)O)C3 LTHGZYQCFFPTAJ-UHFFFAOYSA-N 0.000 description 1
- VIXMOEKUHKZJMV-UHFFFAOYSA-N 2-(1h-imidazol-2-ylamino)acetic acid Chemical compound OC(=O)CNC1=NC=CN1 VIXMOEKUHKZJMV-UHFFFAOYSA-N 0.000 description 1
- SEPZVWYNULYCQA-UHFFFAOYSA-N 2-(1h-pyrrol-2-ylamino)acetic acid Chemical compound OC(=O)CNC1=CC=CN1 SEPZVWYNULYCQA-UHFFFAOYSA-N 0.000 description 1
- KQLGGQARRCMYGD-UHFFFAOYSA-N 2-(cyclobutylamino)acetic acid Chemical compound OC(=O)CNC1CCC1 KQLGGQARRCMYGD-UHFFFAOYSA-N 0.000 description 1
- LRHRHAWNXCGABU-UHFFFAOYSA-N 2-(cyclopentylazaniumyl)acetate Chemical compound OC(=O)CNC1CCCC1 LRHRHAWNXCGABU-UHFFFAOYSA-N 0.000 description 1
- DXQCCQKRNWMECV-UHFFFAOYSA-N 2-(cyclopropylazaniumyl)acetate Chemical compound OC(=O)CNC1CC1 DXQCCQKRNWMECV-UHFFFAOYSA-N 0.000 description 1
- DUJAUTCYDLIGAY-UHFFFAOYSA-N 2-(furan-2-ylamino)acetic acid Chemical compound OC(=O)CNC1=CC=CO1 DUJAUTCYDLIGAY-UHFFFAOYSA-N 0.000 description 1
- SEABHMYCRYLVKD-UHFFFAOYSA-N 2-(naphthalen-2-ylamino)acetic acid Chemical compound C1=CC=CC2=CC(NCC(=O)O)=CC=C21 SEABHMYCRYLVKD-UHFFFAOYSA-N 0.000 description 1
- BKQQPCDQZZTLSE-UHFFFAOYSA-N 2-amino-3-naphthalen-1-ylpropanoic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(CC(N)C(O)=O)=CC=CC2=C1 BKQQPCDQZZTLSE-UHFFFAOYSA-N 0.000 description 1
- ZAQXSMCYFQJRCQ-UHFFFAOYSA-N 3-(1-adamantyl)-2-azaniumylpropanoate Chemical compound C1C(C2)CC3CC2CC1(CC(N)C(O)=O)C3 ZAQXSMCYFQJRCQ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- VCXZJBRVEJBECK-UHFFFAOYSA-N methyl 2,5-dihydropyrrole-1-carboxylate Chemical compound COC(=O)N1CC=CC1 VCXZJBRVEJBECK-UHFFFAOYSA-N 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003147 proline derivatives Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- ZIJTYIRGFVHPHZ-UHFFFAOYSA-N selenium oxide(seo) Chemical class [Se]=O ZIJTYIRGFVHPHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 239000012991 xanthate Substances 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19913699A DE19913699A1 (de) | 1999-03-26 | 1999-03-26 | Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-Dehydropiperidinen |
| TW089104251A TWI276626B (en) | 1999-03-26 | 2000-03-09 | Process for preparing of 3,4-dehydroprolines or 3,4-dehydropiperidines |
| RU2001129097/04A RU2001129097A (ru) | 1999-03-26 | 2000-03-17 | Способ получения n-ацил-3,4-дегидропролина и производных -ацил-3,4-дегидропиперидин-2-карбоновых кислот |
| KR1020017012187A KR20010104730A (ko) | 1999-03-26 | 2000-03-17 | 3,4-데히드로프롤린 및 3,4-데히드로피페리딘의 제조 방법 |
| PCT/EP2000/002377 WO2000058284A1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4 - dehydroprolin und n-acyl-3,4 - dehydropiperidin-2-carbonsäure derivaten |
| AU39625/00A AU3962500A (en) | 1999-03-26 | 2000-03-17 | Method of producing 3,4-dihydroprolines and 3,4-dehydropiperidines |
| TR2001/02747T TR200102747T2 (tr) | 1999-03-26 | 2000-03-17 | N-Asil-3,4-Dihidroprolin ve N-Asil-3,4-Dihidropiperidin-2-Karbonik Asit türevlerinin imalat usulu |
| CA002368479A CA2368479C (en) | 1999-03-26 | 2000-03-17 | Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines |
| IL14552599A IL145525A0 (en) | 1999-03-26 | 2000-03-17 | Method of producing 3,4-dihydroprolines and 3,4-dehydropiperidines |
| DE50008117T DE50008117D1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4-dehydroprolin und n-acyl-3,4-dehydropiperidin-2-carbonsäure derivaten |
| US09/937,312 US6579971B1 (en) | 1999-03-26 | 2000-03-17 | Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines |
| EP00918809A EP1165509B1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4-dehydroprolin und n-acyl-3,4-dehydropiperidin-2-carbonsäure derivaten |
| ES00918809T ES2230088T3 (es) | 1999-03-26 | 2000-03-17 | Procedimiento para la obtrencion de n-acil-3,4-dehidropolina y de derivados del acido n-acil-3,4-dehidropiperidin-2-carboxilico. |
| AT00918809T ATE278665T1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4- dehydroprolin und n-acyl-3,4-dehydropiperidin-2- carbonsäure derivaten |
| HK02106153.8A HK1045156A1 (zh) | 1999-03-26 | 2000-03-17 | N-酰基-3，4-脫氫脯氨酸和n-酰基-3，4-脫氫哌啶-2-羧酸衍生物的製備工藝 |
| JP2000607987A JP3868210B2 (ja) | 1999-03-26 | 2000-03-17 | Ｎ−アシル−３，４−デヒドロプロリンおよびｎ−アシル−３，４−デヒドロピペリジン−２−カルボン酸誘導体の製法 |
| BR0009330-0A BR0009330A (pt) | 1999-03-26 | 2000-03-17 | Processo para preparação de 3,4-deidroprolinas e 3,4-deidropiperidinas |
| CN00805579A CN1345310A (zh) | 1999-03-26 | 2000-03-17 | N－酰基－3,4－脱氢脯氨酸和n－酰基－3,4－脱氢哌啶－2－羧酸衍生物的制备工艺 |
| HU0200420A HUP0200420A2 (hu) | 1999-03-26 | 2000-03-17 | Eljárás 3,4-dehidroprolin- és 3,4-dehidropiperidin-származékok előállítására |
| MXPA01009679A MXPA01009679A (es) | 1999-03-26 | 2000-03-17 | Metodo para producir 3, 4-dihidroprolinas y 3, 4-deshidropiperidinas. |
| CZ20013456A CZ20013456A3 (cs) | 1999-03-26 | 2000-03-17 | Způsob výroby 3,4-dehydroprolinů a 3,4-dehydropiperidinů |
| ZA200107629A ZA200107629B (en) | 1999-03-26 | 2001-09-17 | Method of producing 3,4-dihydroprolines and 3,4-dehydropiperidines. |
| NO20014645A NO20014645L (no) | 1999-03-26 | 2001-09-25 | Fremgangsmåte for fremstilling av 3,4-dihydroproliner og 3,4- dehydropiperidiner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19913699A DE19913699A1 (de) | 1999-03-26 | 1999-03-26 | Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-Dehydropiperidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19913699A1 true DE19913699A1 (de) | 2000-09-28 |
Family
ID=7902464
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19913699A Withdrawn DE19913699A1 (de) | 1999-03-26 | 1999-03-26 | Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-Dehydropiperidinen |
| DE50008117T Expired - Fee Related DE50008117D1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4-dehydroprolin und n-acyl-3,4-dehydropiperidin-2-carbonsäure derivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50008117T Expired - Fee Related DE50008117D1 (de) | 1999-03-26 | 2000-03-17 | Verfahren zur herstellung von n-acyl-3,4-dehydroprolin und n-acyl-3,4-dehydropiperidin-2-carbonsäure derivaten |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6579971B1 (enExample) |
| EP (1) | EP1165509B1 (enExample) |
| JP (1) | JP3868210B2 (enExample) |
| KR (1) | KR20010104730A (enExample) |
| CN (1) | CN1345310A (enExample) |
| AT (1) | ATE278665T1 (enExample) |
| AU (1) | AU3962500A (enExample) |
| BR (1) | BR0009330A (enExample) |
| CA (1) | CA2368479C (enExample) |
| CZ (1) | CZ20013456A3 (enExample) |
| DE (2) | DE19913699A1 (enExample) |
| ES (1) | ES2230088T3 (enExample) |
| HK (1) | HK1045156A1 (enExample) |
| HU (1) | HUP0200420A2 (enExample) |
| IL (1) | IL145525A0 (enExample) |
| MX (1) | MXPA01009679A (enExample) |
| NO (1) | NO20014645L (enExample) |
| RU (1) | RU2001129097A (enExample) |
| TR (1) | TR200102747T2 (enExample) |
| TW (1) | TWI276626B (enExample) |
| WO (1) | WO2000058284A1 (enExample) |
| ZA (1) | ZA200107629B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100396666C (zh) * | 2005-12-14 | 2008-06-25 | 郑州大学 | （4s）-1-叔丁氧羰基-4-氨基-l-脯氨酸乙酯及其合成工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4291040A (en) * | 1979-10-22 | 1981-09-22 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines |
| US5580575A (en) | 1989-12-22 | 1996-12-03 | Imarx Pharmaceutical Corp. | Therapeutic drug delivery systems |
| DE59409568D1 (de) | 1993-09-09 | 2000-11-30 | Schering Ag | Wirkstoffe und gas enthaltende mikropartikel |
| DE19630082A1 (de) * | 1996-07-26 | 1998-01-29 | Basf Ag | Verfahren zur Herstellung von 3-Pyrrolin-2-carbonsäure-Derivaten |
| US6090800A (en) | 1997-05-06 | 2000-07-18 | Imarx Pharmaceutical Corp. | Lipid soluble steroid prodrugs |
| DE19723473A1 (de) * | 1997-06-04 | 1998-12-10 | Basf Ag | Verfahren zur Herstellung von chiralen 3,4-Didehydroprolinen |
| AU753196B2 (en) | 1998-02-09 | 2002-10-10 | Bracco Research S.A. | Targeted delivery of biologically active media |
-
1999
- 1999-03-26 DE DE19913699A patent/DE19913699A1/de not_active Withdrawn
-
2000
- 2000-03-09 TW TW089104251A patent/TWI276626B/zh not_active IP Right Cessation
- 2000-03-17 ES ES00918809T patent/ES2230088T3/es not_active Expired - Lifetime
- 2000-03-17 CN CN00805579A patent/CN1345310A/zh active Pending
- 2000-03-17 WO PCT/EP2000/002377 patent/WO2000058284A1/de not_active Ceased
- 2000-03-17 BR BR0009330-0A patent/BR0009330A/pt not_active IP Right Cessation
- 2000-03-17 MX MXPA01009679A patent/MXPA01009679A/es unknown
- 2000-03-17 IL IL14552599A patent/IL145525A0/xx unknown
- 2000-03-17 RU RU2001129097/04A patent/RU2001129097A/ru unknown
- 2000-03-17 HU HU0200420A patent/HUP0200420A2/hu unknown
- 2000-03-17 TR TR2001/02747T patent/TR200102747T2/xx unknown
- 2000-03-17 HK HK02106153.8A patent/HK1045156A1/zh unknown
- 2000-03-17 EP EP00918809A patent/EP1165509B1/de not_active Expired - Lifetime
- 2000-03-17 KR KR1020017012187A patent/KR20010104730A/ko not_active Abandoned
- 2000-03-17 AT AT00918809T patent/ATE278665T1/de not_active IP Right Cessation
- 2000-03-17 CA CA002368479A patent/CA2368479C/en not_active Expired - Fee Related
- 2000-03-17 CZ CZ20013456A patent/CZ20013456A3/cs unknown
- 2000-03-17 DE DE50008117T patent/DE50008117D1/de not_active Expired - Fee Related
- 2000-03-17 AU AU39625/00A patent/AU3962500A/en not_active Abandoned
- 2000-03-17 US US09/937,312 patent/US6579971B1/en not_active Expired - Lifetime
- 2000-03-17 JP JP2000607987A patent/JP3868210B2/ja not_active Expired - Fee Related
-
2001
- 2001-09-17 ZA ZA200107629A patent/ZA200107629B/en unknown
- 2001-09-25 NO NO20014645A patent/NO20014645L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1165509B1 (de) | 2004-10-06 |
| BR0009330A (pt) | 2002-01-08 |
| RU2001129097A (ru) | 2004-03-20 |
| NO20014645D0 (no) | 2001-09-25 |
| US6579971B1 (en) | 2003-06-17 |
| KR20010104730A (ko) | 2001-11-26 |
| JP2002540190A (ja) | 2002-11-26 |
| DE50008117D1 (de) | 2004-11-11 |
| TR200102747T2 (tr) | 2002-02-21 |
| CA2368479C (en) | 2005-03-01 |
| NO20014645L (no) | 2001-09-25 |
| JP3868210B2 (ja) | 2007-01-17 |
| IL145525A0 (en) | 2002-06-30 |
| CN1345310A (zh) | 2002-04-17 |
| AU3962500A (en) | 2000-10-16 |
| CA2368479A1 (en) | 2000-10-05 |
| ATE278665T1 (de) | 2004-10-15 |
| ES2230088T3 (es) | 2005-05-01 |
| TWI276626B (en) | 2007-03-21 |
| MXPA01009679A (es) | 2002-03-14 |
| WO2000058284A1 (de) | 2000-10-05 |
| CZ20013456A3 (cs) | 2002-05-15 |
| HK1045156A1 (zh) | 2002-11-15 |
| ZA200107629B (en) | 2002-09-17 |
| HUP0200420A2 (hu) | 2002-05-29 |
| EP1165509A1 (de) | 2002-01-02 |
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