GB1304502A - - Google Patents
Info
- Publication number
- GB1304502A GB1304502A GB254671A GB254671A GB1304502A GB 1304502 A GB1304502 A GB 1304502A GB 254671 A GB254671 A GB 254671A GB 254671 A GB254671 A GB 254671A GB 1304502 A GB1304502 A GB 1304502A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- prepared
- phenyl
- hydroxypiperidino
- reaction
- 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.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 5
- 238000006193 diazotization reaction Methods 0.000 abstract 4
- 238000007127 saponification reaction Methods 0.000 abstract 4
- -1 3,3- ethylenedioxy piperidino Chemical group 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- JBVBFRXCWSBOOH-UHFFFAOYSA-N 1,5-dibromopentan-2-ol Chemical compound BrCC(O)CCCBr JBVBFRXCWSBOOH-UHFFFAOYSA-N 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- MOZCOBNPRMGLFD-UHFFFAOYSA-N 1-[2-chloro-4-(1-hydroxypropan-2-yl)phenyl]piperidin-3-one Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)=O)C(CO)C MOZCOBNPRMGLFD-UHFFFAOYSA-N 0.000 abstract 1
- 229940044613 1-propanol Drugs 0.000 abstract 1
- KLLHOJJBWVFBDF-UHFFFAOYSA-N 2-(4-amino-3-chlorophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(N)C(Cl)=C1 KLLHOJJBWVFBDF-UHFFFAOYSA-N 0.000 abstract 1
- FGAFRXFIPDEYKL-UHFFFAOYSA-N 2-(4-bromo-3-nitrophenyl)propan-1-ol Chemical compound [N+](=O)([O-])C=1C=C(C=CC1Br)C(CO)C FGAFRXFIPDEYKL-UHFFFAOYSA-N 0.000 abstract 1
- ZUMGMEDTUNEISY-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZUMGMEDTUNEISY-UHFFFAOYSA-N 0.000 abstract 1
- IVJLGIMHHWKRAN-UHFFFAOYSA-N 2-(chloromethyl)oxolane Chemical compound ClCC1CCCO1 IVJLGIMHHWKRAN-UHFFFAOYSA-N 0.000 abstract 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- NMARDIPDCWDXAY-UHFFFAOYSA-N 2-[3-amino-4-(3-hydroxypiperidin-1-yl)phenyl]propanoic acid Chemical compound NC=1C=C(C=CC1N1CC(CCC1)O)C(C(=O)O)C NMARDIPDCWDXAY-UHFFFAOYSA-N 0.000 abstract 1
- OQWNNBSOUVRUFL-UHFFFAOYSA-N 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]-1-morpholin-4-ylethanethione Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)CC(=S)N1CCOCC1 OQWNNBSOUVRUFL-UHFFFAOYSA-N 0.000 abstract 1
- HRPXGBRJSBLRTB-UHFFFAOYSA-N 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]acetic acid Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)CC(=O)O HRPXGBRJSBLRTB-UHFFFAOYSA-N 0.000 abstract 1
- OWHORRXIEUEMGL-UHFFFAOYSA-N 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]acetonitrile Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)CC#N OWHORRXIEUEMGL-UHFFFAOYSA-N 0.000 abstract 1
- IKJGBLVJUICRJV-UHFFFAOYSA-N 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]propanal Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)C(C=O)C IKJGBLVJUICRJV-UHFFFAOYSA-N 0.000 abstract 1
- MUFUIKGLJKCNRP-UHFFFAOYSA-N 2-[3-chloro-4-(oxolan-2-ylmethylamino)phenyl]propanoic acid Chemical compound ClC=1C=C(C=CC1NCC1CCCO1)C(C(=O)O)C MUFUIKGLJKCNRP-UHFFFAOYSA-N 0.000 abstract 1
- MLDJDYBEOBLSKT-UHFFFAOYSA-N 2-[4-(3-acetyloxypiperidin-1-yl)-3-chlorophenyl]propanoic acid Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)OC(C)=O)C(C(=O)O)C MLDJDYBEOBLSKT-UHFFFAOYSA-N 0.000 abstract 1
- UMICMFHKFJGAJM-UHFFFAOYSA-N 2-[4-(3-hydroxypiperidin-1-yl)phenyl]propanoic acid Chemical compound OC1CN(CCC1)C1=CC=C(C=C1)C(C(=O)O)C UMICMFHKFJGAJM-UHFFFAOYSA-N 0.000 abstract 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 abstract 1
- RVCTZJVBWNFYRU-UHFFFAOYSA-N 4-bromo-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C([N+]([O-])=O)=C1 RVCTZJVBWNFYRU-UHFFFAOYSA-N 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000003529 anticholesteremic agent Substances 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 239000000022 bacteriostatic agent Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 229940030606 diuretics Drugs 0.000 abstract 1
- 239000012374 esterification agent Substances 0.000 abstract 1
- OXWXCOSPMNLBRF-UHFFFAOYSA-N ethene piperidin-3-one Chemical group C=C.N1CC(CCC1)=O OXWXCOSPMNLBRF-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- WPTJMBKBIFEFTA-UHFFFAOYSA-N ethyl 2-(4-amino-3-chlorophenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(N)C(Cl)=C1 WPTJMBKBIFEFTA-UHFFFAOYSA-N 0.000 abstract 1
- OYVYPTCSUQQKCZ-UHFFFAOYSA-N ethyl 2-[3-chloro-4-(1,4-dioxa-9-azaspiro[4.5]decan-9-yl)phenyl]propanoate Chemical compound C(C)OC(C(C)C1=CC(=C(C=C1)N1CC2(CCC1)OCCO2)Cl)=O OYVYPTCSUQQKCZ-UHFFFAOYSA-N 0.000 abstract 1
- SBKRHLWVZFGELU-UHFFFAOYSA-N ethyl 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]-2-hydroxypropanoate Chemical compound C(C)OC(C(C)(C1=CC(=C(C=C1)N1CC(CCC1)O)Cl)O)=O SBKRHLWVZFGELU-UHFFFAOYSA-N 0.000 abstract 1
- HZTQIZUHZGUNFA-UHFFFAOYSA-N ethyl 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]acetate Chemical compound C(C)OC(CC1=CC(=C(C=C1)N1CC(CCC1)O)Cl)=O HZTQIZUHZGUNFA-UHFFFAOYSA-N 0.000 abstract 1
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000871 hypocholesterolemic effect Effects 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 abstract 1
- NWQCZFNCOICPOH-UHFFFAOYSA-N methyl 2-[3-chloro-4-(3-hydroxypiperidin-1-yl)phenyl]propanoate Chemical compound COC(C(C)C1=CC(=C(C=C1)N1CC(CCC1)O)Cl)=O NWQCZFNCOICPOH-UHFFFAOYSA-N 0.000 abstract 1
- ZDPFOIQIGFSVDS-UHFFFAOYSA-N methyl 2-[3-chloro-4-[3-(oxan-2-yloxy)piperidin-1-yl]phenyl]acetate Chemical compound COC(CC1=CC(=C(C=C1)N1CC(CCC1)OC1OCCCC1)Cl)=O ZDPFOIQIGFSVDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000718 radiation-protective agent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 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
- C07D207/12—Oxygen or sulfur 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- C07D207/36—Oxygen or sulfur 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
- C07D211/06—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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702013376 DE2013376A1 (de) | 1970-03-20 | 1970-03-20 | Substituierte Phenylessigsauren und Verfahren zu ihrer Herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1304502A true GB1304502A (enrdf_load_stackoverflow) | 1973-01-24 |
Family
ID=5765732
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB254671A Expired GB1304502A (enrdf_load_stackoverflow) | 1970-03-20 | 1971-01-19 |
Country Status (15)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2114420A1 (de) * | 1971-03-25 | 1972-10-05 | Merck Patent Gmbh, 6100 Darmstadt | Substituierte Phenylalkanol-Derivate und Verfahren zu ihrer Herstellung |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1795036A1 (de) * | 1968-08-01 | 1972-01-20 | Merck Patent Gmbh | p-Aminoarylalkanol-Derivate und Verfahren zu ihrer Herstellung |
CH559755A5 (enrdf_load_stackoverflow) * | 1968-03-27 | 1975-03-14 | Ciba Geigy Ag |
-
1970
- 1970-03-20 DE DE19702013376 patent/DE2013376A1/de active Pending
- 1970-12-07 CH CH1802970A patent/CH556834A/xx not_active IP Right Cessation
-
1971
- 1971-01-19 GB GB254671A patent/GB1304502A/en not_active Expired
- 1971-01-19 ZA ZA710329A patent/ZA71329B/xx unknown
- 1971-01-22 IL IL36044A patent/IL36044A/xx unknown
- 1971-02-16 CS CS1161A patent/CS160138B2/cs unknown
- 1971-02-19 NL NL7102257A patent/NL7102257A/xx unknown
- 1971-03-10 AT AT206371A patent/AT310728B/de not_active IP Right Cessation
- 1971-03-15 PL PL1971146900A patent/PL72098B1/xx unknown
- 1971-03-15 DK DK121471AA patent/DK128077B/da unknown
- 1971-03-17 FR FR7109291A patent/FR2085723B1/fr not_active Expired
- 1971-03-18 SE SE7103514A patent/SE372265B/xx unknown
- 1971-03-18 CA CA108,104A patent/CA973884A/en not_active Expired
- 1971-03-19 BE BE764546A patent/BE764546A/xx unknown
- 1971-03-20 ES ES389399A patent/ES389399A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2085723B1 (enrdf_load_stackoverflow) | 1974-08-23 |
BE764546A (fr) | 1971-09-20 |
IL36044A (en) | 1975-05-22 |
DE2013376A1 (de) | 1971-10-07 |
AT310728B (de) | 1973-10-10 |
IL36044A0 (en) | 1971-03-24 |
NL7102257A (enrdf_load_stackoverflow) | 1971-09-22 |
SE372265B (enrdf_load_stackoverflow) | 1974-12-16 |
CH556834A (de) | 1974-12-13 |
CA973884A (en) | 1975-09-02 |
DK128077B (da) | 1974-02-25 |
CS160138B2 (enrdf_load_stackoverflow) | 1975-02-28 |
FR2085723A1 (enrdf_load_stackoverflow) | 1971-12-31 |
ZA71329B (en) | 1971-10-27 |
PL72098B1 (enrdf_load_stackoverflow) | 1974-06-29 |
ES389399A1 (es) | 1974-03-16 |
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PS | Patent sealed [section 19, patents act 1949] | ||
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